IP Library Granted Patent US 10,287,418
Granted Patent B2
US 10,287,418 · App. 15/371,257 · Granted May 14, 2019

Compounds with antidegradant and antifatigue efficacy and compositions including said compounds

Inventors: Matthew Allen Boone (Gray, TN); Donald L. Fields, Jr. (Copley, OH); Frederick Ignatz-Hoover (Elyria, OH)
Assignee: Eastman Chemical Company
C08K5/18B60C1/00C07C211/54C10L1/223C10L1/2222C10M133/12C10L2230/08C10L2230/081C10M2215/067C10N2230/08C10N2230/10
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Quick Facts
Patent No.
US 10,287,418
App. No.
15/371,257
Granted
May 14, 2019
Kind
B2
Abstract

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

1. An antidegradant composition comprising N,N′-(ethane-1,2-diyl)bis(N-phenylbenzene-1,4-diamine).

2. A lubricant composition comprising a lubricant and the antidegradant composition of claim 1 .

3. A vulcanizable elastomeric formulation comprising an elastomer and the antidegradant composition of claim 1 .

4. The formulation of claim 3 wherein the antidegradant composition is present in an amount of from 0.1 to 20.0 parts per 100 parts elastomer.

5. The formulation of claim 4 wherein the antidegradant composition is present in an amount of from 0.1 to 5.0 parts per 100 parts elastomer.

6. A vulcanized elastomeric article with at least one component formed from the vulcanizable elastomeric formulation of claim 3 .

7. The vulcanized elastomeric article of claim 6 wherein said vulcanized elastomeric article is a vehicle tire.

8. The vehicle tire of claim 7 wherein said component is a sidewall.

9. A combustible fuel composition comprising a combustible fuel and the antidegradant composition of claim 1 .

10. A fuel additive composition comprising a fuel additive and the antidegradant composition of claim 1 .

11. The antidegradant composition of claim 1 , further comprising N,N′-(butane-2,3-diyl)bis(N-phenylbenzene-1,4-diamine).

12. N,N′-(ethane-1,2-diyl)bis(N-phenylbenzene-1,4-diamine).

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: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT AND AS COLLATERAL AGENT
To: FLEXSYS HOLDINGS, INC.
Reel/Frame 071358/0859 →
RELEASE OF SECURITY INTEREST Recorded May 23, 2025
From: RIVER FINANCE HOLDINGS, LLC, AS COLLATERAL AGENT
To: FLEXSYS HOLDINGS, INC.
Reel/Frame 071210/0337 →
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 Apr 21, 2017
From: BOONE, MATTHEW ALLEN; FIELDS, DONALD L., JR.; IGNATZ-HOOVER, FREDERICK
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 042091/0867 →
Continuity (2)
Provisional Application 62270909 · Dec 22, 2015
Related Publication 20170174615A1 · Jun 22, 2017