IP Library Granted Patent US 8,450,446
Granted Patent B2
US 8,450,446 · App. 11/845,410 · Granted May 28, 2013

Rosen phenolic resins and uses related thereto

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Quick Facts
Patent No.
US 8,450,446
App. No.
11/845,410
Granted
May 28, 2013
Kind
B2
Abstract

Rosin modified phenolic resins are prepared by reacting together resin acid, fatty acid, tri- or higher-functional phenolic compound and aldehyde. The fatty acid may be Monomer (derived from the fatty acid dimerization process). The reaction mixture may optionally include a,l3-olefinically unsaturated carbonyl compounds and/or polyol. The resin may be dissolved in a solvent to form a varnish. The resin may be used as a component of printing inks, e.g., inks for lithographic or gravure printing.

Claims (37)

1. A process for preparing a resin, the process comprising reacting reactants at elevated temperature, the reactants comprising fatty acid, wherein at least 10 wt. % of the fatty acid is monomer fatty acid derived from acidic clay polymerization of tall oil fatty acid (Monomer), resin acid, aldehyde, polyol, polyester and phenolic compound that is at least trifunctional with respect to reactivity with aldehyde, where the phenolic compound that is at least trifunctional constitutes at least 25 wt % of all phenolic compounds used to form the resin.

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

3. The process of claim 1 wherein 10 wt. % to 100 wt. % of the fatty acid is Monomer.

4. The process of claim 3 wherein at least 25 wt. % of the fatty acid is Monomer.

5. The process of claim 1 wherein the aldehyde constitutes up to 40 wt % of the reactants.

6. The process of claim 5 wherein the aldehyde constitutes 5-15 wt % of the reactants.

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

8. The process of claim 7 wherein phenolic compound(s) constitute 5-15 wt % of the reactants.

9. The process of claim 1 wherein the aldehyde comprises formaldehyde.

10. The process of claim 1 wherein the polyol constitutes up to 15 wt % of the components.

11. The process of claim 10 wherein the polyol comprises pentaerythritol.

12. The process of claim 1 wherein the reactants further comprise an α,β-olefinically unsaturated carbonyl compound.

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

14. The process of claim 13 wherein the α,β-olefinically unsaturated carbonyl compound comprises maleic anhydride.

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

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

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

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

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

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

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

22. 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.

23. A varnish comprising a resin prepared by the process of claim 1 and a solvent.

24. A process for preparing a resin, the process comprising reacting reactants at elevated temperature, the reactants comprising resin acid, fatty acid, wherein at least 10 wt. % of the fatty acid consists essentially of monomer fatty acid derived from acidic clay polymerization of tall oil fatty acid (Monomer), aldehyde, and phenolic compound that is at least trifunctional with respect to reactivity with aldehyde, where the Monomer contributes at least 5% of the weight of the listed reactants, and the resin has a softening point of at least 105.degree.C, and wherein the phenolic compound that is at least trifunctional constitutes at least 25 wt % of all phenolic compounds used to form the resin.

25. The process of claim 24 wherein the resin has a softening point of at least 120° C.

26. The process of claim 24 wherein 10 wt. % to 100 wt. % of the fatty acid is Monomer.

27. The process of claim 26 wherein at least 25 wt. % of the fatty acid is Monomer.

28. The process of claim 24 wherein phenolic compound that is at least trifunctional with respect to reactivity with aldehyde constitutes at least 5 wt % of all phenolic compounds present among the reactants.

29. The process of claim 24 wherein phenolic compound that is at least trifunctional with respect to reactivity with aldehyde constitutes at least 10 wt % of all phenolic compounds present among the reactants.

30. A resin prepared by the process of claim 1 .

31. The process of claim 3 wherein at least 45 wt. % of the fatty acid is Monomer.

32. The process of claim 3 wherein at least 65 wt. % of the fatty acid is Monomer.

33. The process of claim 3 wherein at least 75 wt. % of the fatty acid is Monomer.

34. The process of claim 26 wherein at least 45 wt. % of the fatty acid is Monomer.

35. The process of claim 26 wherein at least 65 wt. % of the fatty acid is Monomer.

36. The process of claim 26 wherein at least 75 wt. % of the fatty acid is Monomer.

37. A resin prepared the by process of claim 24 .

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 025933/0343 →
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 →