IP Library Granted Patent US 11,667,775
Granted Patent B2
US 11,667,775 · App. 17/160,484 · Granted Jun 6, 2023

Resin-modified vegetable oils in rubber compositions and tires

Inventors: Kelsey Elizabeth Cantwell (Akron, OH); Stephan Rodewald (Dubuque, IA); Joseph John Kulig (Tallmadge, OH); Paul Harry Sandstrom (Cuyahoga Falls, OH)
Assignee: THE GOODYEAR TIRE & RUBBER COMPANY
C08L9/06B60C1/0016C08K5/09C08K5/10C08L91/00C08L93/04
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Quick Facts
Patent No.
US 11,667,775
App. No.
17/160,484
Granted
Jun 6, 2023
Kind
B2
Abstract

The present invention is directed to the use of modified vegetable oils in rubber compositions and in tires.

Claims (14)

1. A vulcanizable rubber composition comprising a vegetable oil derivative comprising the structure

where R 1 , R 2 and R 3 are independently C15-C20 alkenyl, C15-C20 alkyl, and optionally containing aromatic groups; R is —O—C(═O)—R 4 where R 4 is phenyl, alkyl substituted phenyl, hydroxy-substituted phenyl, or terpenoid; each R is covalently bonded to a first carbon atom of one of R 1 , R 2 or R 3 wherein a second carbon atom is adjacent to the first carbon atom and the second carbon atom is substituted with an —OH group; and m ranges from 1 to 5.

2. The vulcanizable rubber composition of claim 1 wherein R is selected from the group consisting of carboxylates of terpenoid carboxylic acids and carboxylates of aromatic carboxylic acids.

3. The vulcanized rubber composition of claim 1 wherein R is selected from the group consisting of carboxylates of abietic acid, neoabietic acid, dehydroabietic acid, palustric acid, levopimaric acid, pimaric acid, and isopimaric acid.

4. The vulcanized rubber composition of claim 1 wherein R is selected from the group consisting of carboxylates of benzoic acid, salicylic acid, para-t-butyl benzoic acid, salicylic acid, 3-hydroxybenzoic acid, and 4-hydroxybenzoic acid.

5. The vulcanizable rubber composition of claim 1 wherein each of R 1 , R 2 , and R 3 are independently at least one member selected from the group consisting of independently at least one member selected from the group consisting of stearyl, palymityl, oleyl, linoleyl, and linolenyl groups.

6. A pneumatic tire comprising the vulcanizable rubber composition of claim 1 .

7. A manufactured item comprising the vulcanizable rubber composition of claim 1 wherein the manufactured item is selected from the group consisting of tire treads, shoes, shoe soles, transmission belts, hoses, airsprings, conveyor belts, track belts, and vibration isolators.

8. A vulcanizable rubber composition comprising the reaction product of an epoxidized vegetable oil and a carboxylic acid selected from the group consisting of terpenoid carboxylic acids and aromatic carboxylic acids.

9. The vulcanizable rubber composition of claim 8 wherein the epoxidized vegetable oil is selected from the group consisting of epoxidized soybean oil, epoxidized canola oil, epoxidized castor oil, epoxidized palm oil, epoxidized sunflower oil, epoxidized coconut oil, and epoxidized corn oil.

10. The vulcanizable rubber composition of claim 8 wherein the terpenoid carboxylic acid is at least one member selected from the group consisting of abietic acid, neoabietic acid, dehydroabietic acid, palustric acid, levopimaric acid, pimaric acid, and isopimaric acid.

11. The vulcanizable rubber composition of claim 8 wherein the aromatic carboxylic acid is at least one member selected from the group consisting of benzoic acid, salicylic acid, para-t-butyl benzoic acid, salicylic acid, 3-hydroxybenzoic acid, and 4-hydroxybenzoic acid.

12. A pneumatic tire comprising the vulcanizable rubber composition of claim 8 .

13. A manufactured item comprising the vulcanizable rubber composition of claim 8 wherein the manufactured item is selected from the group consisting of tire treads, shoes, shoe soles, transmission belts, hoses, airsprings, conveyor belts, track belts, and vibration isolators.

Assignments (4)
SECURITY INTEREST Recorded Dec 10, 2025
From: G-3 CHICKADEE PURCHASER, LLC
To: MIZUHO BANK, LTD., AS ADMINISTRATIVE AGENT
Reel/Frame 073900/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2025
From: THE GOODYEAR TIRE & RUBBER COMPANY
To: G-3 CHICKADEE PURCHASER, LLC
Reel/Frame 073591/0677 →
SECURITY INTEREST Recorded Oct 31, 2025
From: G-3 CHICKADEE PURCHASER, LLC
To: FORTRESS CREDIT CORP., AS ADMINISTRATIVE AGENT
Reel/Frame 073439/0048 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2021
From: CANTWELL, KELSEY ELIZABETH; RODEWALD, STEPHAN; KULIG, JOSEPH JOHN; SANDSTROM, PAUL HARRY
To: THE GOODYEAR TIRE & RUBBER COMPANY
Reel/Frame 055057/0533 →
Continuity (1)
Related Publication 20220235206A1 · Jul 28, 2022