IP Library Granted Patent US 7,207,669
Granted Patent B2
US 7,207,669 · App. 10/742,121 · Granted Apr 24, 2007

Jet printing inks containing polymerized fatty acid-based polyamides

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Quick Facts
Patent No.
US 7,207,669
App. No.
10/742,121
Granted
Apr 24, 2007
Kind
B2
Abstract

The present invention relates to a printing ink composition containing a colorant, resin and solvent, where the resin is a polymerized fatty acid-based polyamide resin and the solvent is made up of at least one first solvent and at least one second solvent, as well as methods of making and using the same.

Claims (47)

1. A method of printing, comprising charging a printhead of an inkjet printer with ink, the ink being a fluid homogeneous mixture comprising polymerized fatty acid-based polyamide resin that is the reaction product of reactants comprising polymerized fatty acid polyamide, ethylene diamine, hexamethylenediamine, and fatty acid with an organic solvent and colorant, wherein the organic solvent comprises a first solvent and a second solvent, where the first solvent comprises at least one solvent selected from solvents comprising a single amide, a single carbamide, or a single hydroxyl group as the only non-hydrocarbon moiety in the solvent; and the second solvent has a viscosity at 25° C. that is less than 60 cps and comprises at least one hydrocarbon solvent; and transferring the ink from the printhead onto a substrate.

2. The method of claim 1 wherein the printer is a drop-on-demand printer.

3. The method of claim 1 wherein the first solvent is at least 20% by weight, and the second solvent is up to 80% by weight of the organic solvent in the ink.

4. The method of claim 1 wherein the first solvent comprises at least one of N-methylpyrrolidinone, N,N-dimethylformamide, N,N-dimethylacetamide, and tetramethylurea; and the second solvent comprises at least one terpene hydrocarbon.

5. The method of claim 1 wherein the first solvent comprises at least one alcohol solvent selected from the group consisting of cyclohexanol, 1-hexanol, 2-hexanol, 3-hexanol, cis-2-hexen-1-ol, trans-2-hexen-1-ol, cycloheptanol, 1-heptanol, 2-heptanol, 2-ethyl-1-hexanol, 1-octanol, 1-nonanol, 3,5,5-trimethyl-1-hexanol, 1-decanol, α-terpineol, and 3,7-dimethyl-3-octanol; and the second solvent comprises mineral spirits or a fraction thereof.

6. The method of claim 1 wherein the organic solvent further comprises a third solvent selected from α-hydroxy-carboxylic ester, polyalkylene glycol alkyl ether, and ketone-containing solvents.

7. The method of claim 6 wherein the third solvent is selected from methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, diethylene glycol methyl ether, dipropylene glycol methyl ether, and cyclohexanone.

8. The method of claim 6 wherein the third solvent is up to 50% by weight of the organic solvent in the ink.

9. A printing ink composition comprising colorant, resin and solvent, where the resin is a polymerized fatty acid-based polyamide resin that is the reaction product of reactants comprising polymerized fatty acid polyamide, ethylene diamine, hexamethylenediamine, and fatty acid, the solvent comprises a first solvent and a second solvent wherein the first solvent comprises at least one solvent having a single amide group or a single carbamide group as the only non-hydrocarbon moiety in the solvent; and the second solvent has a viscosity at 25° C. that is less than 60 cps and comprises at least one hydrocarbon solvent.

10. The printing ink of claim 9 wherein the first solvent is at least 20% by weight, and the second solvent is up to 80% by weight of the organic solvent in the ink.

11. The printing ink of claim 9 wherein the components of the first solvent each have a total of 5 to 11 atoms selected from carbon, nitrogen, and oxygen.

12. The printing ink of claim 11 wherein the first solvent comprises at least one of N-methylpyrrolidinone, N,N-dimethylformamide, N,N-dimethylacetamide, and tetramethylurea.

13. The printing ink of claim 9 wherein the second solvent has a viscosity of less than 45 cps at 25° C.

14. The printing ink of claim 9 wherein the second solvent comprises at least one terpene hydrocarbon.

15. The printing ink of claim 14 wherein the second solvent comprises at least one terpene selected from the group consisting of α-pinene, β-pinene, limionene, and terpinolene.

16. The printing ink of claim 12 or 14 wherein the first solvent comprises at least one of N-methylpyrrolidinone, N,N-dimethylformanide, N,N-dimethylacetamide, and tetramethylurea; and the second solvent comprises at least one terpene hydrocarbon.

17. The printing ink of claim 12 or 14 wherein the first solvent comprises N-methylpyrrolidinone and the second solvent comprises terpinolene.

18. The printing ink of claim 9 wherein the organic solvent further comprises a third solvent selected from α-hydroxy-carboxylic ester, polyalkylene glycol alkyl ether, and ketone.

19. The printing ink of claim 18 wherein the third solvent is selected from methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, diethylene glycol methyl ether, dipropylene glycol methyl ether, and cyclohexanone.

20. The printing ink of claim 18 wherein the third solvent is up to 50% by weight of the organic solvent in the ink.

21. The printing ink of claim 9 wherein the resin comprises 5–40 wt % of the total weight of resin and solvent.

22. The printing ink of claim 9 wherein the solvent comprises at least 30 wt % of the total weight of resin and solvent.

23. The printing ink of claim 9 having a viscosity of less than 25 cps at one or more temperatures between 25° C. and 60° C.

24. The printing ink of claim 9 having a flash point of greater than 40° C.

25. A printing ink composition comprising colorant, resin and solvent, where the resin is a polymerized fatty acid-based polyamide resin that is the reaction product of reactants comprising polymerized fatty acid polyanilde, ethylene diamine, hexamethylenediamine, and fatty acid, the solvent comprises a first solvent and a second solvent, where the first solvent comprises at least one solvent having a single hydroxyl group as the only non-hydrocarbon moiety in the solvent; and the second solvent has a viscosity at 25° C. that is less than 60 cps and comprises at least one hydrocarbon.

26. The printing ink of claim 25 wherein the first solvent is at least 20% by weight, and the second solvent is up to 80% by weight of the organic solvent in the ink.

27. The printing ink of claim 25 wherein the components of the first solvent each have a total of 5 to 11 atoms selected from carbon and oxygen.

28. The printing ink of claim 27 wherein the first solvent comprises a hydroxyl-containing solvent selected from the group consisting of cyclohexanol, 1-hexanol,2-hexanol, 3-hexanol, cis-2-hexen-1-ol, trans-2-hexen-1-ol, cycloheptanol, 1-heptanol, 2-heptanol, 2-ethyl-1-hexanol, 1-octanol, 1-nonanol, 3,5,5-trimethyl-l-hexanol, 1-decanol, α-terpineol, and 3,7-dimethyl-3-octanol.

29. The printing ink of claim 25 wherein the second solvent has a viscosity of less than 45 cps at 25° C.

30. The printing ink of claim 25 wherein the second solvent comprises mineral spirits or a fraction thereof.

31. The printing ink of claim 28 or 30 wherein the first solvent comprises 1-hexanol or 1-heptanol and the second solvent comprises mineral spirits.

32. The printing ink of claim 25 wherein the organic solvent further comprises a third solvent selected from α-hydroxy-carboxylic ester, polyalkylene glycol alkyl ether, and ketone.

33. The printing ink of claim 32 wherein the third solvent is selected from methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, diethylene glycol methyl ether, dipropylene glycol methyl ether, and cyclohexanone.

34. The printing ink of claim 32 wherein the third solvent is up to 50% by weight of the organic solvent in the ink.

35. The printing ink of claim 25 wherein the resin comprises 5–40 wt % of the total weight of resin and solvent in the ink.

36. The printing ink of claim 25 wherein the solvent comprises at least 30 wt % of the total weight of resin and solvent.

37. The printing ink of claim 25 having a viscosity of less than 25 cps at one or more temperatures between 25° C. and 60° C.

38. The printing ink of claim 25 having a flash point of greater than 40° C.

39. The printing ink according to claim 25 , wherein the polymerized fatty acid-based polyamide resin has a softening point of at least 70° C.

40. The printing ink according to claim 25 , wherein the polymerized fatty acid-based polyamide resin has a weight average molecular weight of from 2,000 to 10,000.

41. The method according to claim 1 , wherein the second solvent has a viscosity at 25° C. that is less than 45 cps.

42. The method according to claim 1 , wherein the second solvent has a viscosity at 25° C. that is less than 30 cps

43. The method according to claim 1 , wherein the second solvent has a viscosity at 25° C. that is less than 25 cps.

44. The printing ink according to claim 9 , wherein the second solvent has a viscosity at 25° C. that is less than 30 cps.

45. The printing ink according to claim 9 , wherein the second solvent has a viscosity at 25° C. that is less than 25 cps.

46. The printing ink according to claim 25 , wherein the second solvent has a viscosity at 25° C. that is less than 30 cps.

47. The printing ink according to claim 25 , wherein the second solvent has a viscosity at 25° C. that is less than 25 cps.

Assignments (23)
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NO. 8837224 TO PATENT NO. 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 11, 2022
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 060344/0919 →
RELEASE OF SECURITY INTEREST Recorded Mar 16, 2022
From: BANK OF AMERICA, N.A.
To: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION; KRATON CHEMICAL B.V.
Reel/Frame 059910/0017 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 059366/0727 →
SECURITY INTEREST Recorded Apr 16, 2020
From: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 053020/0101 →
PATENT SECURITY AGREEMENT Recorded Jan 7, 2016
From: ARIZONA CHEMICAL COMPANY, LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 037457/0928 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 8837224 TO PATENT NUMBER 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Jan 6, 2016
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 037448/0453 →
RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Jan 6, 2016
From: ANTARES CAPITAL LP, AS SUCCESSOR TO GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0057 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL AT REEL/FRAME NO. 33146/0361 Recorded Jan 6, 2016
From: GOLDMAN SACHS BANK USA
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0169 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 9, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS RETIRING AGENT
To: ANTARES CAPITAL LP, AS SUCCESSOR AGENT
Reel/Frame 036827/0443 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GOLDMAN SACHS BANK USA, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 033146/0361 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 033146/0333 →
RELEASE OF SECURITY INTEREST Recorded Jun 12, 2014
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 033146/0278 →
SECURITY AGREEMENT Recorded Jan 7, 2012
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 027497/0465 →
RELEASE OF SECURITY INTEREST Recorded Jan 6, 2012
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 027489/0030 →
SECURITY AGREEMENT Recorded Feb 2, 2011
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 025734/0383 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL (FIRST LIEN) Recorded Jan 31, 2011
From: GOLDMAN SACHS CREDIT PARTNERS, L.P.
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 025719/0265 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL (SECOND LIEN) Recorded Jan 31, 2011
From: WILMINGTON TRUST FSB (SUCCESSOR TO CAPITALSOURCE FINANCE LLC)
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 025720/0248 →
CHANGE OF NAME Recorded Nov 24, 2010
From: ARIZONA CHEMICAL COMPANY
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 025406/0597 →
CHANGE OF NAME Recorded Aug 30, 2010
From: CAPITALSOURCE FINANCE LLC
To: WILMINGTON TRUST FSB
Reel/Frame 024944/0501 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: CAPITAL SOURCE FINANCE, LLC
Reel/Frame 019035/0423 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: GOLDMAN SACHS CREDIT PARTNERS, L.P.
Reel/Frame 019035/0392 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 9, 2006
From: INTERNATIONAL PAPER COMPANY
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 018365/0127 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2004
From: PAVLIN, MARK S.
To: INTERNATIONAL PAPER COMPANY
Reel/Frame 015822/0403 →