IP Library Granted Patent US 11,021,581
Granted Patent B2
US 11,021,581 · App. 16/358,078 · Granted Jun 1, 2021

Durable elastomeric compositions employing cyclododecasulfur as a vulcanizing agent

Inventors: Scott Donald Barnicki (Kingsport, TN); Frederick Ignatz-Hoover (Elyria, OH); Robert Thomas Hembre (Johnson City, TN); Andrew Neil Smith (Wadsworth, OH); Henk Kreulen (Halsteren, NL); Aruna M. Velamakanni (Copley, OH); Chenchy Lin (Akron, OH); Ronald H. Arthur (Kingsport, TN)
Assignee: Eastman Chemical Company
C08J3/246C08J3/24C08K3/06C08K5/372C08K5/378C08K5/38C08K5/435C08K5/44C08L21/00B29D30/0601C08J2307/00C08J2309/02C08J2309/06C08K3/04C08L2207/04C08L2312/00
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Quick Facts
Patent No.
US 11,021,581
App. No.
16/358,078
Granted
Jun 1, 2021
Kind
B2
Abstract

Vulcanizable elastomeric formulation are disclosed. The formulations comprise at least one elastomer; a vulcanizing agent comprising cyclododecasulfur; and a prevulcanization inhibitor, present in an amount, for example, from about 0.01 phr to about 10 phr. The formulations, when vulcanized, provide articles that exhibit improved durability.

Claims (21)

1. A vulcanizable elastomeric formulation comprising:

at least one elastomer;

a vulcanizing agent comprising cyclododecasulfur; and

a prevulcanization inhibitor, present in an amount from about 0.01 phr to about 10.0 phr.

2. The vulcanizable elastomeric formulation of claim 1 , wherein the prevulcanization inhibitor comprises one or more of: a sulfenamide, a sulfonamide, a sulfamide, a bis-thioimide, a thiocycloamide, a thioamide, a poly(thioamide), an N-hydrocarbylthio(amide), or a polysulfide.

3. The vulcanizable elastomeric formulation of claim 1 , wherein the prevulcanization inhibitor comprises N-(cyclohexylthiol) phthalimide.

4. The vulcanizable elastomeric formulation of claim 1 , wherein the prevulcanization inhibitor is present in an amount from 0.02 phr to 8 phr.

5. The vulcanizable elastomeric formulation of claim 1 , wherein the prevulcanization inhibitor is present in an amount from 0.05 phr to 5 phr.

6. The vulcanizable elastomeric formulation of claim 1 , wherein the vulcanizable elastomeric formulation further comprises a reinforcing resin, formed of a methylene acceptor and a methylene donor, present in an amount of no more than 2 phr.

7. The vulcanizable elastomeric formulation of claim 1 , wherein the amount of cyclododecasulfur in the formulation is from 1 to 25 phr.

8. The vulcanizable elastomeric formulation of claim 1 , wherein the amount of cyclododecasulfur in the formulation is from 1.5 phr to 20 phr.

9. The vulcanizable elastomeric formulation of claim 1 , wherein the amount of cyclododecasulfur in the formulation is from 2 phr to 15 phr.

10. A vulcanized elastomeric article formed from the vulcanizable elastomeric formulation of claim 1 .

11. A process for forming a vulcanized elastomeric article, comprising:

a) mixing an elastomer with a vulcanizing agent and a prevulcanization inhibitor, present in an amount from about 0.01 phr to about 10.0 phr, to form a vulcanizable elastomeric formulation that includes the vulcanizing agent dispersed in the elastomer; (b) forming the vulcanizable elastomeric formulation into a formed shape; and (c) vulcanizing the formed shape to form the vulcanized elastomeric article; wherein the vulcanizing agent comprises cyclododecasulfur, and wherein at least one of the mixing and forming steps comprises increasing the bulk average processing temperature of said vulcanizable elastomeric formulation to greater than 125° C. for at least a portion of said step.

12. The process of claim 11 , wherein at least one of the mixing and forming steps comprises increasing the bulk average processing temperature of said vulcanizable elastomeric formulation to greater than 128° C. for at least a portion of said step.

13. The process of claim 11 , wherein at least one of the mixing and forming steps comprises increasing the bulk average processing temperature of said vulcanizable elastomeric formulation to greater than 130° C. for at least a portion of said step.

14. The process of claim 11 , wherein said vulcanizable elastomeric formulation further comprises an antireversion agent.

15. The process of claim 14 , wherein said antireversion agent comprises one or more of: hexamethylene-1,6-bis(thiosulfate), disodium salt, dihydrate and 1,3-bis(citraconamidomethyl)benzene.

16. The process of claim 11 , wherein the prevulcanization inhibitor comprises N-(cyclohexylthio) phthalimide.

17. The process of claim 16 , wherein the vulcanized elastomeric article is in the form of a tire.

Assignments (13)
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 Oct 5, 2020
From: FLEXSYS AMERICA L.P.
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 053969/0104 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 2, 2020
From: EASTMAN CHEMICAL MIDDELBURG B.V.
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 053958/0515 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2020
From: IGNATZ-HOOVER, FREDERICK; SMITH, ANDREW NEIL; VELAMAKANNI, ARUNA M.; LIN, CHENCHY; ARTHUR, RONALD H.
To: FLEXSYS AMERICA L.P.
Reel/Frame 053768/0490 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2020
From: BARNICKI, SCOTT DONALD; HEMBRE, ROBERT THOMAS
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 053768/0968 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2020
From: KREULEN, HENK
To: EASTMAN CHEMICAL MIDDELBURG B.V.
Reel/Frame 053768/0037 →