IP Library Granted Patent US 10,550,256
Granted Patent B2
US 10,550,256 · App. 15/666,948 · Granted Feb 4, 2020

Elastomer formulation using a combination of polymers to create ozone resistance without addition of wax

Inventors: Jeanette Pilarski (Amherst, OH); Joshua R. Goossens (Norwalk, OH)
Assignee: The Pullman Company
C08L23/16C08L7/00C08L9/00C08L23/32C08L81/00C08L2205/03C08L2312/00
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Quick Facts
Patent No.
US 10,550,256
App. No.
15/666,948
Granted
Feb 4, 2020
Kind
B2
Abstract

A method for making a vulcanizable rubber composition comprises heating while mixing a first composition comprising EPDM elastomer and alkylphenol disulfide polymer to make a first pass intermediate. The first pass intermediate is combined with a second composition comprising a sulfur crosslinkable natural or synthetic rubber to make a second pass intermediate. The second pass intermediate is combined with a curing package by mixing at a temperature below a curing temperature to make the vulcanizable rubber composition.

Claims (25)

1. A method for making a vulcanizable rubber composition, the method comprising:

heating while mixing a first composition comprising EPDM elastomer and alkylphenol disulfide polymer at a minimum temperature of 165° C. for a time greater than 1 minute and less than 5 minutes to make a first pass intermediate comprising the EPDM elastomer covalently bound to the alkylphenol disulfide polymer;

combining the first pass intermediate with a second composition comprising a sulfur crosslinkable natural or synthetic rubber to make a second pass intermediate; and

combining, with mixing, the second pass intermediate and a curing package comprising ZnO and elemental sulfur to make an uncured vulcanizable rubber composition.

2. The method according to claim 1 , wherein the first composition, the second composition, or both comprise a filler selected from carbon black and silica.

3. The method according to claim 1 , wherein the second composition comprises natural rubber.

4. The method according to claim 1 , wherein the first composition further comprises a sulfur donor.

5. The method according to claim 4 , wherein the sulfur donor is caprolactam disulfide.

6. The method according to claim 1 , wherein the alkylphenol disulfide polymer is poly (t-butylphenol disulfide).

7. The method according to claim 1 , wherein the alkylphenol disulfide polymer is poly (t-amylphenol disulfide).

8. The method according to claim 1 , wherein the first composition is heated to a temperature above the melting point of the alkyl phenol disulfide polymer.

9. The method according to claim 1 , wherein the first composition is heated at 165° C. for over one minute and for less than 5 minutes.

10. A method comprising making a vulcanizable rubber composition by a method according to claim 1 , and applying conditions of temperature for a time sufficient to cure the vulcanizable rubber composition.

11. A method of curing a blend to make an ozone-resistant rubber composition, the method comprising:

applying heat to a blend comprising an EPDM polymer covalently bound to an alkylphenol disulfide polymer, an uncured diene rubber polymer, and a curing package comprising elemental sulfur and ZnO to form the cured ozone-resistant rubber composition,

wherein the uncured rubber polymer is an olefin copolymer having unsaturation in the main chain, and

wherein the EPDM polymer covalently bound to the alkylphenol disulfide polymer is prepared by reacting the EPDM polymer with the alkylphenol disulfide polymer at a minimum temperature of 165° C. for a time greater than 1 minute and less than 5 minutes.

12. The method according to claim 11 , wherein the alkylphenol disulfide polymer is a poly(t-amylphenol disulfide).

13. The method according to claim 11 , wherein the alkylphenol disulfide polymer is a poly(t-butylphenol disulfide).

14. The method according to claim 11 , wherein the EPDM polymer covalently bound to the alkylphenol disulfide polymer is characterized by having a cure rate in the presence of the curing package higher than that of an EPDM polymer without pre-treatment.

15. The method according to claim 11 , wherein the cured blend comprises 10 phr to 50 phr of EPDM.

16. The method according to claim 11 , wherein the cured blend comprises less than 35 phr of EPDM.

17. The method according to claim 11 , wherein the cured blend comprises 25 phr or less of EPDM.

18. The method according to claim 11 , wherein the rubber polymer is selected from natural rubber, polyisoprene, polybutadiene, acrylonitrile polybutadiene, styrene-butadiene, or polychloroprene.

19. The method according to claim 18 , wherein the rubber polymer is natural rubber or polyisoprene.

Assignments (11)
CORRECTIVE ASSIGNMENT TO CORRECT THE CHANGE OF ADDRESS PREVIOUSLY RECORDED ON REEL 72553 FRAME 230. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Feb 11, 2026
From: THE PULLMAN COMPANY
To: THE PULLMAN COMPANY LLC
Reel/Frame 075530/0507 →
CHANGE OF NAME Recorded Aug 20, 2025
From: THE PULLMAN COMPANY
To: THE PULLMAN COMPANY LLC
Reel/Frame 072553/0230 →
PATENT SECURITY AGREEMENT (ABL) Recorded Apr 7, 2023
From: TENNECO INC.; DRIV AUTOMOTIVE INC.; FEDERAL-MOGUL CHASSIS LLC; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL MOTORPARTS LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL WORLD WIDE LLC; TENNECO AUTOMOTIVE OPERATING COMPANY INC.; THE PULLMAN COMPANY
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 063268/0506 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS (FIRST LIEN) Recorded Nov 22, 2022
From: DRIV AUTOMOTIVE INC.; FEDERAL-MOGUL CHASSIS LLC; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL MOTORPARTS LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL WORLD WIDE LLC; TENNECO AUTOMOTIVE OPERATING COMPANY INC.; TENNECO INC.; THE PULLMAN COMPANY
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 061989/0689 →
RELEASE OF SECURITY INTEREST Recorded Nov 19, 2022
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: TENNECO INC.; TENNECO AUTOMOTIVE OPERATING COMPANY INC.; TENNECO INTERNATIONAL HOLDING CORP.; THE PULLMAN COMPANY; TENNECO GLOBAL HOLDINGS INC.; CLEVITE INDUSTRIES INC.; TMC TEXAS INC.; CARTER AUTOMOTIVE COMPANY LLC; FEDERAL-MOGUL WORLD WIDE LLC; FELT PRODUCTS MFG. CO. LLC; MUZZY-LYON AUTO PARTS LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL POWERTRAIN IP LLC; FEDERAL-MOGUL PISTON RINGS, LLC; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL MOTORPARTS LLC; FEDERAL-MOGUL CHASSIS LLC; F-M MOTORPARTS TSC LLC; F-M TSC REAL ESTATE HOLDINGS LLC; FEDERAL-MOGUL VALVE TRAIN INTERNATIONAL LLC; FEDERAL-MOGUL SEVIERVILLE, LLC; BECK ARNLEY HOLDINGS LLC; FEDERAL-MOGUL FILTRATION LLC; FEDERAL-MOGUL FINANCING CORPORATION; FEDERAL-MOGUL PRODUCTS US LLC
Reel/Frame 061975/0218 →
RELEASE OF SECURITY INTEREST Recorded Nov 19, 2022
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: TENNECO INC.; TENNECO AUTOMOTIVE OPERATING COMPANY INC.; THE PULLMAN COMPANY; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL PRODUCTS US LLC; FEDERAL-MOGUL MOTORPARTS LLC; FEDERAL-MOGUL WORLD WIDE LLC; FEDERAL-MOGUL CHASSIS LLC; DRIV AUTOMOTIVE INC.
Reel/Frame 061971/0156 →
RELEASE OF SECURITY INTEREST Recorded Nov 19, 2022
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: TENNECO INC.; TENNECO AUTOMOTIVE OPERATING COMPANY INC.; THE PULLMAN COMPANY; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL PRODUCTS US LLC; FEDERAL-MOGUL WORLD WIDE LLC; FEDERAL-MOGUL CHASSIS LLC; DRIV AUTOMOTIVE INC.
Reel/Frame 061975/0031 →
SECURITY AGREEMENT Recorded Mar 17, 2021
From: TENNECO INC.; TENNECO AUTOMOTIVE OPERATING COMPANY INC.; THE PULLMAN COMPANY; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL PRODUCTS US LLC; FEDERAL-MOGUL WORLD WIDE LLC; FEDERAL-MOGUL CHASSIS LLC; DRIV AUTOMOTIVE INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 055626/0065 →
SECURITY AGREEMENT Recorded Dec 1, 2020
From: TENNECO INC.; THE PULLMAN COMPANY; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL PRODUCTS US LLC; FEDERAL-MOGUL MOTORPARTS LLC; FEDERAL-MOGUL WORLD WIDE LLC; FEDERAL-MOGUL CHASSIS LLC; DRIV AUTOMOTIVE INC.; TENNECO AUTOMOTIVE OPERATING COMPANY INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 054555/0592 →
CONFIRMATORY GRANT OF SECURITY INTERESTS IN UNITED STATES PATENTS Recorded Oct 9, 2018
From: TENNECO INC.; TENNECO AUTOMOTIVE OPERATING COMPANY INC.; TENNECO INTERNATIONAL HOLDING CORP.; THE PULLMAN COMPANY; TENNECO GLOBAL HOLDINGS INC.; CLEVITE INDUSTRIES INC.; TMC TEXAS INC.; CARTER AUTOMOTIVE COMPANY LLC; FEDERAL-MOGUL WORLD WIDE LLC; FELT PRODUCTS MFG. CO. LLC; MUZZY-LYON AUTO PARTS LLC; FEDERAL-MOGUL POWERTRAIN LLC; FEDERAL-MOGUL POWERTRAIN IP LLC; FEDERAL-MOGUL PISTON RINGS, LLC; FEDERAL-MOGUL IGNITION LLC; FEDERAL-MOGUL MOTORPARTS LLC; FEDERAL-MOGUL CHASSIS LLC; F-M MOTORPARTS TSC LLC; F-M TSC REAL ESTATE HOLDINGS LLC; FEDERAL-MOGUL VALVETRAIN INTERNATIONAL LLC; FEDERAL-MOGUL SEVIERVILLE, LLC; BECK ARNLEY HOLDINGS LLC; FEDERAL-MOGUL FILTRATION LLC; FEDERAL-MOGUL FINANCING CORPORATION; FEDERAL-MOGUL PRODUCTS US LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL TRUSTEE
Reel/Frame 047223/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2017
From: PILARSKI, JEANETTE; GOOSSENS, JOSHUA R.
To: THE PULLMAN COMPANY
Reel/Frame 043171/0877 →
Continuity (2)
Provisional Application 62382332 · Sep 1, 2016
Related Publication 20180057672A1 · Mar 1, 2018