IP Library Patent Application 18794397
Patent Application
App. No. 18/794,397

METHOD FOR COLD FLOW REDUCTION OF ELASTOMERS

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Patent No.
US None
App. No.
18/794,397
Abstract

A method for the synthesis of an elastomer comprising the steps of polymerizing conjugated diene monomer in presence of at least one rare earth transition metal catalyst system to generate a polydiene cement; terminating the polydiene cement with a protic organic compound; connecting polymer chains by reacting (1) a compound containing sulfur and a halogen with (2) an hydroxyethyl alkenyl ether/hydroxypropyl alkenyl ether; and adding a product of the reaction to the cement to generate a polydiene rubber.

Claims (22)

1 . A method for the synthesis of an elastomer comprising the steps of:

polymerizing conjugated diene monomer to generate a polydiene cement;

terminating the polydiene cement with a protic organic compound followed by a previously prepared additive comprising: (1) a compound containing sulfur and a halogen and (2) a hydroxyethyl alkenyl ether or hydroxypropyl alkenyl ether.

2 . The method of claim 1 , wherein the hydroxyethyl alkenyl ether comprises at least one unsaturated carbon-carbon bond and one hydroxyl group.

3 . The method of claim 1 , wherein the hydroxypropyl alkenyl ether comprises at least one unsaturated carbon-carbon bond and one hydroxyl group.

4 . The method of claim 1 , wherein the compound containing sulfur and a halogen is disulfur dichloride (S 2 Cl 2 ), sulfur dichloride, disulfur dibromide, sulfur dibromide, thionyl chloride, thionyl bromide or a combination thereof.

5 . The method of claim 1 , wherein the hydroxyethyl alkenyl ether is 2-(allyloxy)ethanol, 2-[2-(allyloxy)ethoxy]ethanol, 2-(vinyloxy)ethanol, and 2-[2-(vinyloxy)ethoxy]ethanol or a combination thereof.

6 . The method of claim 1 , wherein the hydroxypropyl alkenyl ether is 1-(allyloxy)-2-propanol, 1-(vinyloxy)-2-propanol, or a combination thereof.

7 . The method of claim 4 , wherein the reaction between the S 2 Cl 2 and hydroxyethyl alkenyl ether/hydroxypropyl alkenyl ether is performed in the range of −15° C. to 100° C.

8 . The method of claim 4 , wherein the reaction between the S 2 Cl 2 and hydroxyethyl alkenyl ether/hydroxypropyl alkenyl ether uses a solvent.

9 . The method of claim 4 , wherein the reaction between the S 2 Cl 2 and hydroxyethyl alkenyl ether/hydroxypropyl alkenyl ether excludes a solvent.

10 . The method of claim 3 , wherein a mole ratio between (1) the compound containing sulfur and a halogen and (2) the hydroxyethyl alkenyl ether/hydroxypropyl alkenyl ether bearing at least one unsaturated carbon-carbon bond is between 3:1 to 1:2.

11 . The method of claim 1 , wherein the total amount of the hydroxyethyl alkenyl ether/hydroxypropyl alkenyl ether is from 0.5 mmol to 5.5 mmol per 100 grams of the polydiene cement.

12 . The method of claim 1 , wherein the elastomer is characterized by an increase of at least 13% in cold flow resistance compared to the elastomer without the addition of (1) the compound containing sulfur and a halogen and (2) the hydroxyethyl alkenyl ether/hydroxypropyl alkenyl ether.

13 . The method of claim 1 , wherein the polymer is prepared by:

polymerizing conjugated diene monomer at temperatures of 25° C. to 125° C. in presence of at least one rare earth transition metal catalyst system based on neodymium carboxylate or neodymium phosphate, a saturated aliphatic or alicyclic organic hydrocarbon solvent, an alkylating agent based on aluminum, and organometallic halogen source to generate the polydiene cement.

14 . The method of claim 13 , wherein the elastomer having at least 90% 1,4-cis content.

15 . The method of claim 1 , wherein polymerizing the conjugated diene monomer comprises:

polymerizing a conjugated diene monomer compound in the presence of alkyl lithium and a modifier to generate the polydiene cement.

16 . The method of claim 1 , wherein polymerizing the conjugated diene monomer comprises:

polymerizing a conjugated diene monomer compound and styrene in the presence of alkyl lithium and a modifier to generate the polydiene cement.

17 . A tire having a tread or carcass compound comprising at least the 1,4-cis polydiene of claim 1 .

Assignments (4)
SECURITY INTEREST Recorded Dec 10, 2025
From: G-3 CHICKADEE PURCHASER, LLC
To: MIZUHO BANK, LTD., AS ADMINISTRATIVE AGENT
Reel/Frame 073900/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2025
From: THE GOODYEAR TIRE & RUBBER COMPANY
To: G-3 CHICKADEE PURCHASER, LLC
Reel/Frame 073484/0873 →
SECURITY INTEREST Recorded Oct 31, 2025
From: G-3 CHICKADEE PURCHASER, LLC
To: FORTRESS CREDIT CORP., AS ADMINISTRATIVE AGENT
Reel/Frame 073439/0048 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2024
From: MESGAR, MILAD; MURRAY, AARON PATRICK; DENT, PETER ISAAC; VIELHABER, MARGARET FLOOK
To: THE GOODYEAR TIRE & RUBBER COMPANY
Reel/Frame 068190/0226 →