IP Library Granted Patent US 9,109,073
Granted Patent B1
US 9,109,073 · App. 14/462,967 · Granted Aug 18, 2015

Bifunctionalized polymer

Inventors: Liqing Ma (Uniontown, OH); Paul Harry Sandstrom (Cuyahoga Falls, OH); Arindam Mazumdar (Stow, OH)
Assignee: The Goodyear Tire & Rubber Company
C08F36/08C08F12/08C08F36/06
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Quick Facts
Patent No.
US 9,109,073
App. No.
14/462,967
Granted
Aug 18, 2015
Kind
B1
Abstract

The present invention is directed to a bifunctionalized elastomer comprising the reaction product of (1) a living anionic elastomeric polymer initiated with a functional initiator and (2) a functional polymerization terminator.

Claims (24)

1. A bifunctionalized elastomer comprising the reaction product of 1) a living anionic elastomeric polymer initiated with a functional initiator and 2) a functional polymerization terminator, wherein

1) the living anionic elastomeric polymer initiated with a functional initiator is of formula AYLi where Y is a divalent polymer radical, Li is a lithium atom bonded to a carbon atom of Y, and A is an amine-containing radical having the formula X

wherein R 15 and R 16 independently have from 1 to 20 carbon atoms and each are independently an alkyl group, a cycloalkyl group, an aromatic group, a substituted alkyl group, a substituted cycloalkyl group or a substituted aromatic group, or R 15 and R 16 taken together with the nitrogen to which both R 15 and R 16 are attached comprise a heterocyclic amine group wherein R 15 and R 16 taken together form an alkanediyl group of from 4 to 20 carbon atoms or a substituted alkanediyl group of from 4 to 20 carbon atoms, and R 17 is a covalent bond, an alkanediyl group of from 1 to 20 carbon atoms or a substituted alkanediyl group of from 1 to 20 carbon atoms; and

2) the functional polymerization terminator is of formula I

wherein R 1 is C1 to C4 linear alkyl, or C1 to C4 branched alkanediyl;

X 1 , X 2 , X 3 are independently O, S, or a group of formula (II) or (III)

where R 2 is C1 to C18 linear or branched alkyl; Z is R 3 , —OR 4 , or —R 5 —X 4 ; R 3 , R 4 are independently C1 to C18 linear or branched alkyl; R 5 is C1 to C18 alkanediyl or dialkyl ether diyl; X 4 is halogen or a group of structure IV, V, VI, VII or VIII

wherein R 6 , R 7 , R 8 , R 9 , and R 10 are independently H or C1 to C8 alkyl; R 11 is C2 to C8 alkanediyl; R 12 and R 13 are independently H, aryl or C1 to C8 alkyl; Q is N or a group of structure IX

wherein R 14 is C1 to C8 alkyl.

2. The functionalized elastomer of claim 1 , wherein the living anionic elastomer is derived from at least one diene monomer and optionally at least one vinyl aromatic monomer.

3. The functionalized elastomer of claim 1 , wherein the living anionic elastomer is derived from at least one of isoprene and butadiene, and optionally from styrene.

4. The functionalized elastomer of claim 1 , wherein the living anionic elastomer is derived from butadiene and styrene.

5. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I is ESTI, 1-ethoxy-3,7,10-trimethylsilatrane.

6. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I is CSTI, 1-(3-chloropropyl)-3,7,10-trimethylsilatrane.

7. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I is BSTI, 1-isobutyl-3,7,10-trimethylsilatrane.

8. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I is OSTI, 1-octyl-3,7,10-trimethylsilatrane.

9. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I is BIPOS, 1,2-bis(3,7,10-trimethylsilatrane)ethane.

10. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I is selected from the group consisting of the following structures

11. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I has the structure

12. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I has the structure

13. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I has the structure

14. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I has the structure

15. The functionalized elastomer of claim 1 , wherein the structure of formula X is selected from the group consisting of 3-(N,N-dimethylamino)-1-propyl, 3-(N,N-dimethylamino)-2-methyl-1-propyl, 3-(N,N-dimethylamino)-2,2-dimethyl-1-propyl, 4-(N,N-dimethylamino)-1-butyl, 5-(N,N-dimethylamino)-1-pentyl, 6-(N,N-dimethylamino)-1-hexyl, and 8-(N,N-dimethylamino)-1-propyl.

16. The functionalized elastomer of claim 1 , wherein the structure of formula X is selected from the group consisting of 3-piperidino-1-propyl and 3-pyrrolidino-1-propyl.

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 7, 2025
From: THE GOODYEAR TIRE & RUBBER COMPANY
To: G-3 CHICKADEE PURCHASER, LLC
Reel/Frame 073591/0677 →
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 19, 2014
From: MA, LIQING; SANDSTROM, PAUL HARRY; MAZUMDAR, ARINDAM
To: GOODYEAR TIRE & RUBBER COMPANY, THE
Reel/Frame 033563/0434 →