IP Library Granted Patent US 6,875,842
Granted Patent B2
US 6,875,842 · App. 10/402,348 · Granted Apr 5, 2005

Resinates from monomer

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Quick Facts
Patent No.
US 6,875,842
App. No.
10/402,348
Granted
Apr 5, 2005
Kind
B2
Abstract

Reduced-rosin compositions of printing inks and the resinate binders therein, and the processes of preparation thereof, are described. In said compositions, a portion of the rosin normally used in the art is replaced by Monomer, and is further reacted with α,β-unsaturated carboxylic compound, alkaline metal salt, and solvent to produce the resinate binder product. Said resinate binder may then be formulated with a colorant to produce an ink, preferably for use in publication gravure.

Claims (45)

1. A resinate composition comprising the reaction product of reactants, the reactants comprising:

(a) rosin;

(b) Monomer; and

(c) metal salt, the metal salt comprising a metal cation, the metal selected from Group IIA or Group IIB metals of the Periodic Table.

2. The composition of claim 1 wherein the reactants comprise about 5-85 wt % rosin, about 1-50 wt % Monomer, and about 1-15 wt % metal salt, based on the total weight of the reactants.

3. The composition of claim 1 wherein the reactants comprise acid equivalents attributed to fatty arid and acid equivalents attributed to rosin, and Monomer contributes about 55-1% of the total acid equivalents attributed to rosin and fatty acid.

4. The composition of claim 3 wherein Monomer contributes 35-10% of the total acid equivalents attributed to rosin and fatty acid.

5. The composition of claim 1 wherein the reactants comprise acid equivalents attributed to Monomer and acid equivalents attributed to rosin, and the ratio of acid equivalents attributed to rosin:acid equivalents attributed to Monomer is in the range of about 0.5:1 to 15:1.

6. The composition of claim 5 wherein the range is 1:1 to 5:1.

7. The composition of claim 1 wherein the reactants further comprise α,β-unsaturated carboxylic compound, tall oil fatty acid, or a combination thereof.

8. The composition of claim 7 wherein the reactants comprise at least one of:

(a) about 1-25 wt % α,β-unsaturated carboxylic compound, and

(b) up to about 2 wt % tall oil fatty acid;

where the wt % values are based on the total weight of the reactants.

9. The composition of claim 1 wherein the reactants further comprise maleic anhydride, the metal is a mixture of calcium and magnesium, and the composition comprises toluene.

10. The composition of claim 1 further comprising a solvent selected from one or a combination of an inorganic solvent and an organic solvent, wherein the organic solvent does not contain a hydroxyl, aldehyde, alkenyl, cycloalkenyl, or nitrogen-containing group.

11. The composition of claim 1 wherein the reactants further comprise a reactant selected from the group consisting of polyhydric alcohol, phenolic resin, phenolic compound, aldehyde, and mixtures thereof.

12. The composition of claim 11 wherein the reactants comprise at least one of:

(a) up to about 25 wt % polyhydric alcohol;

(b) up to about 50 wt % phenolic compound; and

(c) up to about 40 wt % aldehyde;

where the wt % values are based on the total weight of the reactants.

13. A process for preparing a resinate composition comprising the steps of

(a) melting rosin in a reaction vessel, optionally in admixture with Monomer;

(b) charging the reaction vessel with Monomer if Monomer is not already present in the reaction vessel;

(c) charging the reaction vessel with a metal salt comprising a cation selected from Group IIA or Group IIB of the Periodic Table, and optionally solvent, to provide a reaction mixture;

(d) incubating the reaction mixture at elevated temperature to produce a reaction product; and

(e) cooling the reaction product (e) to yield a resinate composition.

14. The process of claim 13 wherein the composition is prepared from reactants, the reactants comprising about 5-85 wt % rosin, about 1-50 wt % Monomer, and about 1-15 wt % metal salt, based on the total weight of reactants, and 0-80 wt % solvent based on the weight of the composition.

15. The process of claim 13 further comprising adding to the reaction vessel at least one of:

(a) up to about 25 wt % polyhydric alcohol;

(b) up to about 50 wt % phenolic compound; and

(c) up to about 40 wt % aldehyde;

where the wt % values are based on the total weight of reactants charged to the reaction vessel.

16. The process of claim 13 wherein the resinate composition is prepared by a fusion method.

17. The process of claim 16 wherein the reaction vessel is charged with about 20-85 wt % rosin, about 1-50 wt % Monomer, about 1-15 wt % alkaline metal salt, up to about 30 wt % hydrocarbon solvent, up to about 5 wt % lower organic acid, and 0-5 wt % water.

18. The process of claim 16 further comprising

(a) charging the reaction vessel with phenolic compound;

(b) charging the reaction vessel with formaldehyde.

19. The process of claim 16 further comprising charging the reaction vessel with polyhydric alcohol.

20. A resinate composition formed by the process of claim 13 .

21. A resinate composition prepared by the process of claim 16 .

22. In a process for preparing a metal resinate of rosin, the improvement comprising substituting up to about 55 acid equivalent percent of the rosin with Monomer.

23. A printing ink comprising pigment and the resinate composition of claim 1 .

24. A printing ink varnish comprising the resinate composition of claim 1 .

Assignments (22)
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 →
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 →
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 →
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 →
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 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: GOLDMAN SACHS CREDIT PARTNERS, L.P.
Reel/Frame 019035/0392 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: CAPITAL SOURCE FINANCE, LLC
Reel/Frame 019035/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2003
From: FONTANA, THOMAS A.
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 014156/0505 →