IP Library › Granted Patent US 8,703,849
Granted Patent B2
US 8,703,849 · App. 13/519,956 · Granted Apr 22, 2014

Processes for making high purity renewable source-based plasticizers and products made therefrom

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Quick Facts
Patent No.
US 8,703,849
App. No.
13/519,956
Granted
Apr 22, 2014
Kind
B2
Abstract

Presently disclosed are high purity unsaturated fatty acid esters with an ester moiety characterized by having from five to seven members in a ring structure, which esters when epoxidized find particular utility as primary plasticizers in flexible polyvinyl halide applications. Also disclosed are processes for making the high purity esters.

Claims (12)

1. A polyvinyl halide composition comprising a polyvinyl halide polymer and an epoxidized soyate ester composition of the combined epoxidized esters of the fatty acids in soybean oil, in which the ester moiety is characterized by a five to seven member ring structure, which epoxidized soyate ester composition contains not more than about 5.0 percent by weight of monoglycerides and diglycerides combined.

2. A polyvinyl halide composition according to claim 1 , wherein the epoxidized soyate ester composition contains not more than about 2.0 percent by weight of monoglycerides and diglycerides.

3. A polyvinyl halide composition according to claim 2 , wherein the epoxidized soyate ester composition contains not more than about 0.4 percent by weight of monoglycerides and diglycerides.

4. A polyvinyl halide composition according to claim 3 , wherein the epoxidized soyate ester composition contains not more than about 0.25 percent by weight of monoglycerides and diglycerides.

5. A polyvinyl halide composition according to claim 1 , wherein the epoxidized soyate ester composition predominantly comprises the epoxidized benzyl esters of the fatty acids in soybean oil.

6. A polyvinyl halide composition according to any of claims 1 , 2 , 3 , 4 or 5 , wherein the epoxidized soyate ester composition is used as a primary plasticizer component.

7. A polyvinyl halide composition according to claim 6 , wherein the epoxidized soyate ester composition is not less than about 20 percent by weight of the polyvinyl halide composition.

8. A polyvinyl halide composition according to claim 7 , wherein the epoxidized soyate ester composition is from about 20 to about 50 percent by weight of the polyvinyl halide composition.

9. A polyvinyl halide composition according to claim 8 , wherein the epoxidized soyate ester composition is from about 30 to about 50 percent by weight of the polyvinyl halide composition.

10. A polyvinyl halide composition according to claim 8 , wherein the epoxidized soyate ester composition is from about 40 to about 50 percent by weight of the polyvinyl halide composition.

11. A polyvinyl halide composition according to claim 10 , further comprising an epoxidized vegetable oil as a secondary plasticizer.

12. A polyvinyl halide composition according to claim 11 , which is plasticized only by the epoxidized soyate ester composition as a primary plasticizer and an epoxidized vegetable oil secondary plasticizer.

Assignments (13)
RELEASE OF SECURITY INTERESTS IN PATENTS RECORDED AT REEL 037101, FRAME 0448. Recorded Jun 24, 2025
From: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
To: AVIENT CORPORATION (F/K/A POLYONE CORPORATION); COLORMATRIX HOLDINGS, INC.
Reel/Frame 071730/0746 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Aug 18, 2021
From: CERBERUS BUSINESS FINANCE AGENCY, LLC
To: ECHO US HOLDINGS, LLC
Reel/Frame 057221/0585 →
CHANGE OF NAME Recorded Oct 29, 2019
From: ECHO US HOLDINGS, LLC
To: GEON PERFORMANCE SOLUTIONS, LLC
Reel/Frame 050860/0746 →
PARTIAL RELEASE OF SECURITY INTEREST RECORDED AT R/F 037101/0448 Recorded Oct 28, 2019
From: WELLS FARGO CAPITAL FINANCE LLC
To: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.
Reel/Frame 050838/0181 →
PARTIAL RELEASE OF SECURITY INTEREST RECORDED AT R/F/ 037146/0724 Recorded Oct 28, 2019
From: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
To: POLYONE CORPORATION
Reel/Frame 050838/0320 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2019
From: POLYONE CORPORATION
To: ECHO US HOLDINGS, LLC
Reel/Frame 050847/0396 →
ASSIGNMENT FOR SECURITY -- PATENTS Recorded Oct 25, 2019
From: ECHO US HOLDINGS, LLC
To: CERBERUS BUSINESS FINANCE AGENCY, LLC
Reel/Frame 050829/0840 →
RELEASE OF SECURITY INTEREST IN PATENTS AT REEL/FRAME 037113/0144 Recorded Mar 23, 2018
From: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.
Reel/Frame 045680/0342 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPLICATION NUMBER 14/501,050 PREVIOUSLY RECORDED ON REEL 037101 FRAME 0448. ASSIGNOR(S) HEREBY CONFIRMS THE PATENT SECURITY AGREEMENT. Recorded Jan 27, 2016
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 037603/0208 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPL. NO. 14/501,050 PREVIOUSLY RECORDED AT REEL: 037113 FRAME: 0144. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY AGREEMENT. Recorded Jan 7, 2016
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 037508/0012 →
SECURITY AGREEMENT Recorded Nov 19, 2015
From: POLYONE CORPORATION; COLORMATRIX GROUP, INC.; COLORMATRIX HOLDINGS, INC.; THE COLORMATRIX CORPORATION; GAYSON SILICONE DISPERSIONS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: CITIBANK, N.A,, AS ADMINISTRATIVE AGENT
Reel/Frame 037146/0724 →
PATENT SECURITY AGREEMENT Recorded Nov 16, 2015
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 037113/0144 →
SECURITY INTEREST Recorded Nov 12, 2015
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 037101/0448 →