IP Library Granted Patent US 10,407,562
Granted Patent B2
US 10,407,562 · App. 16/103,080 · Granted Sep 10, 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
C08K5/18B60C1/00C07C209/18C07C211/54C10L1/223C10L1/2222C10M133/12C10L2230/08C10L2230/081C10M2215/067C10N2230/08C10N2230/10
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Quick Facts
Patent No.
US 10,407,562
App. No.
16/103,080
Granted
Sep 10, 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 (16)

1. A compound represented by the formula:

wherein R is substituted or unsubstituted aryl;

wherein X 1 , X 2 , X 3 and X 4 are each hydrogen; and

wherein one of R 1 and R 2 and one of R 3 and R 4 is methyl, and one of R 1 and R 2 and one of R 3 and R 4 is hydrogen.

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

3. N,N′-(1,3-phenylenebis(ethane-1,1-diyl))bis(N-phenylbenzene-1,4-diamine).

4. An antidegradant composition comprising the compound of claim 1 and a carrier for the compound.

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

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

7. The formulation of claim 6 , wherein the compound is present in an amount of from 0.1 to 20.0 parts per 100 parts of elastomer.

8. The formulation of claim 6 , wherein the compound is present in an amount of from 0.1 to 5.0 parts per 100 parts of elastomer.

9. A vulcanized elastomeric article comprising the vulcanizable elastomeric formulation of claim 6 .

10. The vulcanized elastomeric article of claim 9 , wherein the vulcanized elastomeric article is a vehicle tire.

11. The vehicle tire of claim 10 , wherein the component is a sidewall.

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

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

Assignments (8)
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 →
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 Aug 14, 2018
From: BOONE, MATTHEW ALLEN; FIELDS, DONALD L., JR.; IGNATZ-HOOVER, FREDERICK
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 046796/0493 →
Continuity (3)
Continuation 15371257 · Dec 7, 2016
Provisional Application 62270909 · Dec 22, 2015
Related Publication 20180355148A1 · Dec 13, 2018