Bridgestone Corporation

Bridgestone/firestone, Inc.

Bridgestone Corportion

Mark L Stayer, Jr

David F Lawson

Thomas A Antkowiak

John R Schreffler

Hideki Komatsu

Russell W Koch

Yoichi Ozawa

Koichi Morita

H James Harwood

Ryota Fujio

A vulcanizable elastomeric compound and products such as pneumatic tires and the like, are formed from a functionalized polymer having a functional group derived from an anionic polymerization initiator. The anionic polymerization initiator comprises the general formula ##STR1## where R.sup.1 -R.sup.5 are the same or different and are selected from the group consisting of hydrogen; alkyls having from alkyls having from 1 to about 12 carbon atoms; aralkyls having from 7 to about 20 carbon atoms; dialkylaminos having from 2 to about 20 carbon atoms; and, dialkylaminoalkyls having from 3 to about 20 carbon atoms. At least one of R.sup.1 -R.sup.5 is selected from the group consisting of the dialkylaminos and the dialkylaminoalkyls. Methods of the present invention include preparing functionalized polymers and reducing the hysteresis of vulcanizable elastomeric compounds.

Functionalized polymer of improved hysteresis properties prepared using

Low-hysteresis elastomer compositions using amino-substituted

A terminally functionalized liquid polymer is prepared by reacting a low molecular weight living diene polymer or copolymer obtained by anionic polymerization of a diene monomer or mixture of a diene monomer and a vinyl aromatic hydrocarbon monomer with a fused-ring polynuclear aromatic compound. The resultant terminally functionalized liquid diene polymers or copolymers can be utilized as dispersants for particulates such as carbon black or graphite and may also be employed as viscosity modifiers for lubricating oils or in electrorheological devices or damping devices.

Liquid diene polymers and copolymers terminated by reaction with

The present invention is directed toward anionic polymerization initiators which are soluble in acyclic alkane solvents. The initiators include a solubilized lithio amine having the general formula (A)Li(SOL).sub.y. SOL is a solubilizing component and A is an alkyl, dialkyl or cycloalkyl amine radical or a cyclic amine and y is from about 1 to 4. The invention is also directed toward polymers and other products made using the initiator, and methods therefore. Further, the invention contemplates a polymer, a polymer composition and products therefrom, which include a functional group from the reaction product of an amine and an organolithium compound. The resulting polymers may be terminated with a terminating, coupling or linking agent, which may provide the polymer with a multifunctionality.

Solubilized anionic polymerization initiator and preparation thereof

The present invention is directed toward anionic polymerization initiators which are soluble in hydrocarbon solvents. The initiators include a lithio amine having the general formula ALi. The component A is a dialkyl or dicycloalkyl amine radical or a cyclic amine. The invention is also directed toward polymers and other products made using the initiator, and methods therefor. Further, the invention contemplates a polymer, a polymer composition and products therefrom, which include a functional group from the reaction product of an amine and an organolithium compound. The resulting polymers may be terminated with a terminating, coupling or linking agent, which may provide the polymer with a multifunctionality.

Soluble anionic polymerization initiators and preparation thereof

Diene polymers or copolymers having improved raw polymer viscosity and reduced hysteresis in the cured and carbon black reinforced state are provided. These diene polymers or copolymers are prepared by a method which involves first terminating substantially all of the living diene polymer or copolymer chains obtained by anionic polymerization with a compound having multiple-bonded nitrogen atoms selected from the group consisting of aromatic nitriles and substituted imines having the formula ##STR1## and then coupling a portion of the resultant terminated polymer chains with a polyfunctional reagent selected from the groups consisting of silicon polyhalides, polyisocyanates, phosphoryl halides and polycarboxylic acid halides.

Diene polymers and copolymers terminated with compounds having

Amino-substituted aryllithium compounds as anionic polymerization

An anionic polymerization initiator comprising the reaction product of a functionalizing agent selected from the group consisting of substituted aldimines, ketimines and secondary amines and, an organolithium compound. Elastomeric polymers prepared with these initiators have functional sites incorporated at the initiator end of the polymer chain and provide vulcanizable rubber compounds exhibiting reduced hysteresis. Articles such as tires, produced with low hysteresis elastomeric polymers have lower rolling resistance. Methods are also provided for preparing the initiators, functionalized polymers and vulcanizable elastomeric compounds having reduced hysteresis.

Elastomers and products having reduced hysteresis

Diene polymers or copolymers having improved raw polymer viscosity and reduced hysteresis in the cured and carbon black reinforced state are provided. These diene polymers or copolymers comprise a mixture of diene polymer or copolymer chains containing carbon-tin bonds in the main polymer or copolymer chains and diene polymer or copolymer chains containing terminals derived from aromatic nitrile coumpounds. The diene polymer or copolymers are prepared by first coupling a portion of the living diene polymer or copolymer chains obtained by anionic polymerization using a tin polyhalide coupling agent and then terminating the remaining living diene polymer or copolymer chains using aromatic nitrile compounds. The resultant diene polymers or copolymers have improved raw polymer viscosity and when compounded with carbon black and cured have reduced hysteresis properties. The polymers can be utilized to form elastomer compositions for tire treads having reduced rolling resistance.

Diene polymers having reduced hysteresis and improved raw viscosity

Diene polymer or copolymer compositions having reduced hysteresis are provided. The compositions comprise a mixture of diene polymers or copolymers containing carbon-tin bonds in the main polymer or copolymer chains prepared by coupling polymer or copolymer chains with tin polyhalides and diene polymers or copolymer chains containing terminals derived from substituted imines having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of H, alkyl, cycloalkyl, aryl, dialkylaminoaryl, aralkyl and aprotic O, N and S- containing alkyl, cycloalkyl, aryl and aralkyl groups; wherein R.sub.3 is selected from the group consisting of alkyl, cycloalkyl, aryl, dialkylaminoaryl, aralkyl and aprotic O, N, and S- containing alkyl, cycloalkyl, aryl and aralkyl groups; with the proviso that at least one of the R.sub.1, R.sub.2 and R.sub.3 groups must be a dialkylaminoaryl group and that not all of the R.sub.1, R.sub.2 and R.sub.3 groups must be a dialkylaminoaryl group and that not all of the R.sub.1, R.sub.2 and R.sub.3 groups must be a dialkylaminoaryl group and that not all of the R.sub.1, R.sub.2 and R.sub.3 groups can be aryl groups. The resultant diene polymer or copolymer compositions have reduced hysteresis and improved processability and can be utilized to form elastomer compositions for tire treads having reduced rolling resistance.

Diene polymers and copolymers jumped by partial crosslinking and

A terminally functionalized polymer is prepared by reacting a living polymer obtained by anionic polymerization of a diene monomer or mixture of a diene monomer and a vinyl aromatic hydrocarbon monomer with a fused-ring polynuclear aromatic compound. The resultant terminally functionalized polymers have reduced hysteresis in the carbon black reinforced and cured state and can be utilized to form elastomer compositions for tire treads having reduced rolling resistance.

Diene polymers and copolymers terminated by reaction with fused-ring

Diene polymers or copolymers having improved raw polymer viscosity and reduced hysteresis in the cured and carbon black reinforced state are provided. These diene polymers or copolymers comprise a mixture of diene polymer or copolymer chains containing carbon-tin bonds in the main polymer or copolymer chains and diene polymer or copolymer chains containing terminals derived from fused-ring polynuclear aromatic compounds. The diene polymer or copolymers are prepared by first coupling a portion of the living diene polymer or copolymer chains obtained by anionic polymerization using a tin polyhalide coupling agent and then terminating the remaining living diene polymer or copolymer chains using fused-ring polynuclear aromatic compounds. The resultant diene polymers or copolymers have improved raw polymer viscosity and when compounded with carbon black and cured have reduced hysteresis properties. The polymers can be utilized to form elastomer compositions for tire treads having reduced rolling resistance.

A terminally functionalized polymer is prepared by reacting a living polymer obtained by anionic polymerization of a diene monomer or mixture of a diene monomer and a vinyl aromatic hydrocarbon monomer with an aromatic nitrile compound. Especially useful aromatic nitriles are the unsubstituted and substituted benzonitriles. The resultant terminally functionalized polymers have reduced hysteresis in the carbon black reinforced and cured state and can be utilized to form elastomer compositions for tire treads having reduced rolling resistance.

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Mogadore, OH, United States of America

Mark L Stayer, Jr