The Goodyear & Tire Rubber Company

Other

Margaret Flook Vielhaber

Stefan Mecking

Seth Cody Ensign

Hannes Leicht

Inigo Gottker Genannt Schnetmann

Inigo Göttker-Schnetmann

Philip Kenyon

Julia Bauer

Liqing Ma

Jena Lynn Johngrass

Julia Katharina Bauer

The compatibility between silica fillers and synthetic rubbers which are synthesized utilizing lanthanide-based catalyst systems, such as neodymium catalyst systems can be improved by terminating the polymerization with a vinyl silane terminating agent. In doing so the vinyl silane is allowed to react with the polymer chain ends of the neodymium rubber to functionalize the chain ends of the polymer chains with silicon containing groups. This results in the rubber having better characteristics for utilization in tire rubber formulations, such a tire tread formulations, that exhibit improved wear characteristics and lower rolling resistance. The process for the synthesis of such functionalized polydiene rubber comprises (1) polymerizing a diene monomer in the presence of a lanthanide-based catalyst system, and (2) terminating the polymerization with a vinyl silane terminator. The functionalized polydiene rubber composition made by this method is comprised of a polydiene rubber which is functionalized at its chain ends with a silicon containing group.

Silicon-functionalized rubber

The present invention is directed to a method of making a functionalized elastomer, comprising the step of polymerizing a conjugated diene monomer in the presence of a lanthanide-based coordination polymerization catalyst activated with a functionalized aluminum reagent of formula 1 where R is a linear or branched alkane group containing 1 to 8 carbon atoms, and Ris phenylene, or a linear or branched alkane diyl group containing 2 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; Q is of formula 2 where R, Rand Rare independently a linear or branched alkyl group containing 1 to 3 carbon atoms or a group of formula 3 where R3 and R4 are independently phenyl or a linear or branched alkyl group containing 1 to 10 carbon atoms, or R3 and R4 taken together with the nitrogen atom represent a nitrogen containing heterocyclic group containing from 4 to 12 carbon atoms; or R, Rand Rtaken together with the silicon atom represent a structure of formula 4 where Ris C1 to C4 linear or branched alkanediyl and Z is N or a group of formula 5 wherein Ris C1 to C8 alkyl.

Method of making a functionalized elastomer, elastomer, rubber composition and tire

The invention is directed to functionalized aluminum reagents of formula 1 where R is a linear or branched alkane group containing 1 to 8 carbon atoms, and Ris phenylene, or a linear or branched alkane diyl group containing 2 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; Q is of formula 2 where R, Rand Rare independently a linear or branched alkyl group containing 1 to 3 carbon atoms or a group of formula 3 where Rand Rare independently phenyl or a linear or branched alkyl group containing 1 to 10 carbon atoms, or Rand Rtaken together with the nitrogen atom represent a nitrogen containing heterocyclic group containing from 4 to 12 carbon atoms; or R, Rand Rtaken together with the silicon atom represent a structure of formula 4 where Ris C1 to C4 linear or branched alkanediyl and Z is N or a group of formula 5 wherein Ris C1 to C8 alkyl.

Functionalized aluminum reagents

The invention is directed to functionalized aluminum reagents of formula 1 where R is a linear or branched alkane group containing 1 to 8 carbon atoms, and Ris phenylene, or a linear or branched alkane diyl group containing 2 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; Q is of formula 2 where Rand Rare independently phenyl or a linear or branched alkyl group containing 1 to 10 carbon atoms, or Rand Rtaken together with the nitrogen atom represent a nitrogen containing heterocyclic group containing from 4 to 12 carbon atoms.

The present invention is directed to a method of making a functionalized elastomer, comprising the step of polymerizing a conjugated diene monomer in the presence of a lanthanide-based coordination polymerization catalyst activated with a functionalized aluminum reagent of formula 1 where R is a linear or branched alkane group containing 1 to 8 carbon atoms, and R1 is phenylene, or a linear or branched alkane diyl group containing 2 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; Q is of formula 2 where R3 and R4 are independently phenyl or a linear or branched alkyl group containing 1 to 10 carbon atoms, or R3 and R4 taken together with the nitrogen atom represent a nitrogen containing heterocyclic group containing from 4 to 12 carbon atom.

The present invention is directed to a stereoregular functionalized elastomer represented by poly(M1 co M2), wherein the functionalized elastomer comprises a microstructure selected from the group consisting of microstructures having at least 90 percent by weight of monomer residues in trans 1,4-configuration, and microstructures having at least 80 percent by weight of monomer residues in cis 1,4-configuration; wherein M1 is selected from the group consisting of isoprene and 1,3-butadiene; and M2 is of formula 4 wherein Ris a covalent bond, phenylene, a linear or branched alkane diyl group containing 1 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; Ris hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; Xis selected from formulas 5 and 6 wherein Rand Rare independently trialkylsilyl, phenyl or a linear or branched alkyl group containing 1 to 10 carbon atoms, or one of Rand Ris hydrogen and the other is phenyl or a linear or branched alkyl group containing 1 to 10 carbon atoms, or Rand Rtaken together with the nitrogen atom represent a nitrogen containing heterocyclic group containing from 4 to 12 carbon atoms; and Xis a sulfur atom or a structure of formula 7 or 8 wherein when Xis of formula 8, the S atom of formula 8 is adjacent to the phenyl ring of formula 6 and the N atom of formula 8 is adjacent to R.

Functionalized elastomer

The present invention is directed to a method of making a functionalized elastomer, comprising the step of polymerizing monomers comprising a conjugated diene monomer in the presence of a lathanide-based coordination polymerization catalyst activated with a magnesium compound of formula 1   

Growing community of inventors

Kent, OH, United States of America

Margaret Flook Vielhaber