IP Library Granted Patent US 8,158,743
Granted Patent B2
US 8,158,743 · App. 11/741,536 · Granted Apr 17, 2012

Rosin phenolic resins for printing inks

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Quick Facts
Patent No.
US 8,158,743
App. No.
11/741,536
Granted
Apr 17, 2012
Kind
B2
Abstract

Rosin modified phenolic resins are prepared by reacting together rosin, fatty acid, phenol and aldehyde. The fatty acid may be Monomer (derived from the fatty acid dimerization process). The reaction mixture may optionally include α,β-olefinically unsaturated carboxylic acid(s) or anhydride(s), and polyol(s). The resin may be dissolved in a solvent to form a varnish. The resin may be used as a component of inks for lithographic or gravure printing.

Claims (28)

1. A process for preparing a resin, the process comprising reacting components at elevated temperature, the components comprising rosin, a fatty acid source, aldehyde and phenolic compound, wherein said fatty acid source consists essentially of Tall Oil Fatty Acids, and where phenol constitutes at least 25 wt % of the phenolic compounds, wherein the resin comprises a melting point from 120.degree.C. to 200.degree.C. and an acid number greater than 50 and less than 70.

2. The process of claim 1 wherein phenol constitutes at least 35 wt % of the phenolic compounds.

3. The process of claim 1 wherein phenol constitutes at least 55 wt % of the phenolic compounds.

4. The process of claim 1 wherein the rosin constitutes up to 85 wt % of the components.

5. The process of claim 1 wherein the fatty acid source constitutes up to 65 wt % of the components.

6. The process of claim 1 wherein the aldehyde constitutes up to 40 wt % of the components.

7. The process of claim 1 wherein phenolic compound(s) including phenol constitute up to 50 wt % of the components.

8. The process of claim 1 wherein the aldehyde component comprises formaldehyde.

9. The process of claim 1 wherein the rosin component comprises gum rosin.

10. The process of claim 1 wherein the components further comprise polyol.

11. The process of claim 10 wherein the polyol component constitutes up to 15 wt % of the components.

12. The process of claim 1 wherein the components further comprise an .alpha.,.beta.-unsaturated carbonyl compound.

13. The process of claim 12 wherein the .alpha.,.beta.-unsaturated carbonyl compound constitutes up to 8 wt % of the components.

14. The process of claim 1 wherein the resin is self-gelling in mineral oil at resin:mineral oil weight ratio of 1:1.5.

15. The process of claim 1 wherein the resin is completely soluble in mineral oil at 10% solids at 180.degree.C.

16. The process of claim 1 wherein the resin has a softening point in excess of 120.degree.C.

17. The process of claim 1 wherein a 45 wt % solution of the resin in a hydrocarbon solvent has a flow viscosity at 25.degree.C. of 0.1 to 150 pascal-seconds.

18. The process of claim 1 wherein the resin is suitable for use as a lithographic ink resin.

19. The process of claim 1 wherein the resin is suitable for use as a gravure ink resin.

20. The process of claim 1 wherein azeotropic distillation is not used to remove water from the resin.

21. The process of claim 1 wherein an inert organic solvent capable of azeotropic distillation of water at the elevated temperature is not used as an entraining agent for azeotropic distillation of water.

22. An oil-soluble resin prepared by the process of any of claim 1 - 7 or 8 - 21 .

23. A varnish comprising an oil-soluble resin prepared by the process of any of claim 1 - 7 or 8 - 22 , and a solvent.

24. The varnish of claim 23 wherein the solvent is a hydrocarbon.

25. A lithographic ink comprising a resin of claim 22 .

26. A gravure ink comprising a resin of claim 22 .

27. A process for preparing an oil-soluble resin, the process comprising reacting components at elevated temperature, the components comprising rosin, aldehyde, phenolic compound and a fatty acid source consisting essentially of the fraction of the distillation product of the acid clay catalyzed polymerization product of Tall Oil Fatty Acid that is highly enriched in monomeric fatty acids, where the fatty acid source constitutes at least 30 wt % of the components,

wherein the oil-soluble resin comprises a melting point from 120.degree.C. to 200.degree.C. and an acid number greater than 50 and less than 70.

Assignments (15)
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 15, 2022
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 059366/0727 →
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 →
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 →
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 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 →
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 INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 033146/0333 →
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 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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 10, 2011
From: FONTANA, THOMAS A.
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 025933/0707 →
SECURITY AGREEMENT Recorded Feb 2, 2011
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 025734/0383 →
CHANGE OF NAME Recorded Nov 24, 2010
From: ARIZONA CHEMICAL COMPANY
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 025406/0597 →