IP Library Granted Patent US 8,013,046
Granted Patent B2
US 8,013,046 · App. 11/708,645 · Granted Sep 6, 2011

Methods of vulcanizing elastomers using tall oil heads

Assignee: Arizona Chemical Company, LLC
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Quick Facts
Patent No.
US 8,013,046
App. No.
11/708,645
Granted
Sep 6, 2011
Kind
B2
Abstract

Tall oil heads may be used in lieu of, or in combination with, conventional fatty acids in the compounding and curing of vulcanizable rubber. Tall oil heads inherently contain a significant amount of neutral materials, and their incorporation into a pre-vulcanized rubber composition allows the compounder to incorporate less aromatic oil into the composition. The composition may be made by a method comprising compounding a mixture comprising a vulcanizable elastomer, a sulfur source, and Tall Oil Heads (TOH), the TOH comprising 40-75 wt % fatty acids and greater than 10 wt % neutral materials, and heating the compounded mixture to a temperature sufficient to cause substantial crosslinking of the elastomer.

Claims (23)

1. A method for making a cross-linked elastomer which comprises compounding a mixture comprising a vulcanizable elastomer, a sulfur source, and Tall Oil Heads (TOH), the TOH comprising 40 to just under 90 wt % fatty acids and greater than 10 wt % unsaponifiable materials, wherein said TOH comprises palmitic acid as the predominant fatty acid and heating the compounded mixture to a temperature sufficient to cause substantial crosslinking of the elastomer.

2. A method for making a cross-linked elastomer which comprises compounding a mixture comprising a vulcanizable elastomer, a sulfur source, and from about 0.1 to about 6.0% by weight of Tall Oil Heads (TOH), and heating the compounded mixture to a temperature sufficient to cause substantial crosslinking of the elastomer wherein said TOH comprises palmitic acid as the predominant fatty acid.

3. A method of enhancing the cure of a sulfur vulcanizable elastomer selected from the group consisting of natural rubber, synthetic rubber or mixture thereof which comprises adding Tall Oil Heads (TOH) to a sulfur vulcanizable elastomer to provide an admixture, and heating the admixture to a temperature sufficient to achieve vulcanization, wherein said TOH comprises palmitic acid as the predominant fatty acid.

4. A method of enhancing the cure of a sulfur vulcanizable elastomer selected from the group consisting of natural rubber, synthetic rubber or mixture thereof which comprises adding a distillation fraction of Tall Oil Heads (TOH) to a sulfur vulcanizable elastomer to provide an admixture, and heating the admixture to a temperature sufficient to achieve vulcanization, wherein the distillation fraction comprises at least 50 wt % palmitic acid.

5. The method of any one of claims 1 - 4 wherein said elastomer is selected from the group consisting of natural rubber, neoprene, polyisoprene, butyl rubber, polybutadiene, styrene-butadiene copolymer, styrene/isoprene/butadiene rubber, methyl methacrylate-butadiene copolymer, isoprene-styrene copolymer, methyl methacrylate-isoprene copolymer, acrylonitrile-isoprene copolymer, acrylonitrile-butadiene copolymer, EPDM and mixtures thereof.

6. The method of any one of claims 1 - 4 wherein the TOH comprises at least one terpene selected from the group α-pinene, β-pinene, camphene, 3-carene, and 1-terpineol.

7. The method of any one of claims 1 - 4 wherein the TOH comprises at least one hydrocarbon selected from β-cadinene and retene.

8. The method of any one of claims 1 - 4 wherein the TOH contains at least 0.2 wt % 3,5-dimethoxystilbene (DMS).

9. The method of any one of claims 1 - 4 wherein the TOH contains a phenolic material selected from phenol, guaiacol, ethylguaiacol, hydroeugenol, eugenol, cis-isoeugenol, trans-isoeugenol and acetoguaiacol.

10. The method of any one of claims 1 - 4 wherein the TOH has an acid number in the range, of 100-175.

11. The method of any one of claims 1 - 4 wherein 95 wt % of the TOH has a boiling point of less than, about 223° C. at 8-12 mm Hg pressure.

12. The method of claim 4 wherein the distillation fraction from TOH has a palmitic acid content of at least 75 wt %.

13. The method of claim 4 wherein the distillation fraction from TOH has an acid number within the range of 150-220.

14. A compounded mixture for preparing a cross-linked elastomer, the mixture comprising a vulcanizable elastomer, a sulfur source, and Tall Oil Heads (TOH), the TOH comprising unsaponifiables and fatty acids where the weight of the unsaponifiable fraction exceeds 10% based on the total weight of the TOH, and wherein said TOH comprises palmitic acid as the predominant fatty acid.

15. A compounded mixture for preparing a cross-linked elastomer, the mixture comprising a vulcanizable elastomer, a sulfur source, and a distillation fraction from Tall Oil Heads (TOH), the TOH comprising unsaponifiables and fatty acids where the weight of the unsaponifiable fraction exceeds 10% based on the total weight of the TOH, and wherein said TOH comprises palmitic acid as the predominant fatty acid.

16. The mixture of claim 14 or 15 wherein said elastomer is selected from the group consisting of natural rubber, neoprene, polyisoprene, butyl rubber, polybutadiene, styrenebutadiene copolymer, styrene/isoprene/butadiene rubber, methyl methacrylate-butadiene copolymer, styrene-styrene copolymer, methyl methacrylate-isoprene copolymer, acrylonitrileisoprene copolymer, acrylonitrile-butadiene copolymer, EPDM and mixtures thereof.

17. The mixture of claim 14 or 15 wherein the TOH comprises at least one terpene selected from the group α-pinene, β-pinene, camphene, 3-carene, and 1-terpineol.

18. The mixture of claim 14 or 15 wherein the TOH contains at least 0.2 wt % 3,5-dimethoxystilbene (DMS).

19. The mixture of claim 15 wherein the distillation fraction from TOH contains at least 50% palmitic acid based on the total weight of the distillation fraction.

20. The mixture of claim 15 wherein the distillation fraction from TOH has a palmitic acid content of at least 75 wt %.

21. The mixture of claim 14 or 15 wherein the TOH has an acid number in the range of 100-175.

22. The mixture of claim 14 or 15 wherein the TOH has a boiling point of less than about 223° C. at 8-12 mm Hg pressure.

23. The mixture of claim 14 wherein the TOH has an acid number in the range of 150-220.

Assignments (14)
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 →
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 →
Continuity (3)
Continuation 10573098
Provisional Application 60267594 · Feb 8, 2001
Related Publication 20070260018A1 · Nov 8, 2007