IP Library Granted Patent US 10,260,017
Granted Patent B2
US 10,260,017 · App. 15/618,281 · Granted Apr 16, 2019

Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including said compounds

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Quick Facts
Patent No.
US 10,260,017
App. No.
15/618,281
Granted
Apr 16, 2019
Kind
B2
Abstract

A compound represented by the formula: wherein each R is independently selected from the group consisting of (i) substituted or unsubstituted alkyl with C=0 to 12 inclusive; wherein X 1 , X 2 , X 3 and X 4 are each independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; and wherein one of R 1 and R 2 and one of R 3 and R 4 may optionally be bridged by a polymethylene group to form a cycloalkyl; wherein when C=0 in R, the combined group R 1 R 2 is the same as the combined group R 3 R 4 ; and wherein when C=1 in R, each of R 1 , R 2 , R 3 , and R 4 are hydrogen.

Claims (22)

1. A compound represented by the formula:

wherein R is selected from the group consisting of a substituted or unsubstituted alkyl with C=0 to 3 inclusive;

wherein X 1 , X 2 , X 3 and X 4 are each independently selected from the group consisting of hydrogen or methyl; and

wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of propyl, ethyl, methyl, or hydrogen, and wherein one of R 1 and R 2 and one of R 3 and R 4 are bridged by a polymethylene group to form a cycloalkyl.

2. The compound of claim 1 , wherein R is selected from the group consisting of a substituted or unsubstituted alkyl with C=0 to 2.

3. The compound of claim 1 , wherein R is selected from the group consisting of a substituted or unsubstituted alkyl with C=1 to 2.

4. The compound of claim 1 , wherein R is selected from the group consisting of a substituted or unsubstituted alkyl with C=1 to 3.

5. The compound of claim 1 , wherein one of R 1 and R 2 and one of R 3 and R 4 are bridged by a polymethylene group to form a cyclohexane group.

6. The compound of claim 1 , wherein one of R 1 and R 2 and one of R 3 and R 4 are bridged by a polymethylene group to form a cyclobutane group.

7. The compound of claim 1 , wherein one of R 1 and R 2 and one of R 3 and R 4 are bridged by a polymethylene group to form a cyclopentane group.

8. An antidegradant composition comprising the compound of claim 1 and optionally a carrier for said compound.

9. A lubricant composition comprising a lubricant and the compound of claim 1 .

10. A vulcanizable elastomeric formulation comprising an elastomer and the compound of claim 1 .

11. The formulation of claim 10 wherein said the compound is present in an amount of from 0.1 to 20.0 parts per 100 parts elastomer.

12. The formulation of claim 11 wherein said the compound is present in an amount of from 0.1 to 5.0 parts per 100 parts elastomer.

13. A vulcanized elastomeric article with at least one component formed from the vulcanizable elastomeric formulation of claim 10 .

14. The vulcanized elastomeric article of claim 13 wherein said vulcanized elastomeric article is a vehicle tire.

15. The vehicle tire of claim 14 wherein said component is a sidewall.

16. A combustible fuel composition comprising a combustible fuel and the compound of claim 1 .

17. A fuel additive composition comprising a fuel additive and the compound of claim 1 .

18. The compound of claim 1 , wherein one of R 1 and R 2 and one of R 3 and R 4 are bridged by a polymethylene group to form a cycloheptane group.

19. The compound of claim 1 , wherein one of R 1 and R 2 and one of R 3 and R 4 are bridged by a polymethylene group to form a cyclooctane group.

Assignments (9)
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY DATA AND PROPERTY NUMBERS PREVIOUSLY RECORDED ON REEL 71519 FRAME 647. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 27, 2025
From: FLEXSYS HOLDINGS, INC.
To: FLEXSYS IP HOLDINGS, LLC
Reel/Frame 071784/0643 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2025
From: FLEXSYS HOLDINGS, INC.
To: FLEXSYS IP HOLDINGS, LLC
Reel/Frame 071519/0647 →
SECURITY INTEREST Recorded May 28, 2025
From: FLEXSYS IP HOLDINGS, LLC
To: ROYAL BANK OF CANADA, AS THE COLLATERAL AGENT
Reel/Frame 071243/0123 →
RELEASE OF SECURITY INTEREST Recorded May 23, 2025
From: RIVER FINANCE HOLDINGS, LLC, AS COLLATERAL AGENT
To: FLEXSYS HOLDINGS, INC.
Reel/Frame 071210/0337 →
RELEASE OF SECURITY INTEREST Recorded May 23, 2025
From: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT AND AS COLLATERAL AGENT
To: FLEXSYS HOLDINGS, INC.
Reel/Frame 071358/0859 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Dec 27, 2024
From: FLEXSYS HOLDINGS, INC.
To: RIVER FINANCE HOLDINGS, LLC, AS COLLATERAL AGENT
Reel/Frame 069791/0623 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2022
From: EASTMAN CHEMICAL COMPANY
To: FLEXSYS HOLDINGS, INC.
Reel/Frame 060423/0395 →
SECURITY INTEREST Recorded Nov 1, 2021
From: FLEXSYS HOLDINGS, INC.
To: ROYAL BANK OF CANADA
Reel/Frame 057978/0662 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 14, 2017
From: BOONE, MATTHEW ALLEN; FIELDS, DONALD L., JR.; IGNATZ-HOOVER, FREDERICK
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 043585/0463 →