Patents by Inventor Thomas Antkowiak
Thomas Antkowiak has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5785778Abstract: A functionalized polymer according to the invention includes a polymer molecule having the general formula AYLi where A is a cyclic amine-containing radical having the general formula ##STR1## wherein R.sub.1 is a divalent alkylene, an oxy- or amino-alkylene, or substituted alkylene having from 6 to about 20 carbon atoms; R.sub.2 is a linear-, branched-, or cyclo-alkylene having from about 2 to about 20 carbon atoms; and Y is a divalent polymer radical and Li is a lithium atom bonded to a carbon atom of Y.Type: GrantFiled: March 7, 1997Date of Patent: July 28, 1998Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
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Patent number: 5730910Abstract: A method of preparing polymetalated compositions and the use of such polymetalated compounds as catalysts in polymerization reactions are described. The process comprises reacting (A-1) an allenic compound of the formula R.sup.2 --CH.dbd.C.dbd.CH.sub.2 wherein R.sup.2 is hydrogen or an aliphatic group containing from 1 to about 10 carbon atoms with (A-2) an organometallic compound R.sup.o M in a mole ratio of about 1:2 to about 1:6 wherein R.sup.o is a hydrocarbyl group and M is an alkali metal.A method of preparing a hydrocarbon-soluble polymetalated compositions also is described, and this process comprises the steps of(A) preparing an intermediate by reacting (A-1) an allenic compound of the formula R.sup.2 --CH.dbd.C.dbd.CH.sub.2 wherein R.sup.2 is hydrogen or an aliphatic group containing from 1 to about 10 carbon atoms with (A-2) an organometallic compound R.sup.o M in a mole ratio of about 1:2 to about 1:6 wherein R.sup.Type: GrantFiled: January 3, 1997Date of Patent: March 24, 1998Assignee: Bridgestone/Firestone, Inc.Inventor: Thomas A. Antkowiak
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Patent number: 5610237Abstract: A functionalized polymer according to the invention includes a polymer molecule having the general formula AYLi where A is a cyclic amine-containing radical having the general formula ##STR1## wherein R.sub.1 is a divalent alkylene, an oxy- or amino-alkylene, or substituted alkylene having from 6 to about 20 carbon atoms; R.sub.2 is a linear-, branched-, or cyclo-alkylene having from about 2 to about 20 carbon atoms; and Y is a divalent polymer radical and Li is a lithium atom bonded to a carbon atom of Y.Type: GrantFiled: June 4, 1996Date of Patent: March 11, 1997Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
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Patent number: 5610228Abstract: An anionic polymerization initiator includes a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A method of preparing an anionic polymerization initiator includes reacting an excess of a cyclic secondary amine with a conjugated diene to form an adduct; and, reacting the adduct with an organolithium compound. A method of preparing a polymer includes forming a solution of one or more anionically polymerizable monomers in a hydrocarbon solvent; and, polymerizing the monomer with an anionic polymerization initiator comprising a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A functionalized polymer includes the termination product of a living polymer having the general formula AYLi, wherein A is a functional group derived from an anionic polymerization initiator; and, Y is a divalent polymer radical; wherein the anionic polymerization initiator is a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene.Type: GrantFiled: June 6, 1995Date of Patent: March 11, 1997Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr.
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Patent number: 5610227Abstract: The present invention provides anionic polymerization initiators, comprising lithium amino magnesiate complexes, resulting in diene polymer and copolymer elastomers. The invention initiators have stable living ends at high polymerization temperatures and produce polymers containing a high level of tertiary amine functionality. Such polymers exhibit an increased efficiency in coupling termination reactions, and elastomers and products prepared from such polymers exhibit reduced hysteresis properties. Methods are also provided for preparing the initiators, the polymers and the elastomers.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignee: Bridgestone/Firestone, Inc.Inventors: Thomas A. Antkowiak, James E. Hall
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Patent number: 5574109Abstract: A functionalized polymer according to the invention includes a polymer molecule having the general formula AYLi where A is a cyclic amine-containing radical having the general formula ##STR1## R.sub.1 is a divalent alkylene, an oxy- or amino-alkylene, or substituted alkylene having from 6 to about 20 carbon atoms; R.sub.2 is a linear-, branched-, or cyclo-alkylene having from about 2 to about 20 carbon atoms; and Y is a divalent polymer radical and Li is a lithium atom bonded to a carbon atom of Y.Type: GrantFiled: February 1, 1995Date of Patent: November 12, 1996Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
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Patent number: 5567815Abstract: An anionic initiator system formed by the reaction product of: (1) an organolithium compound with (2) the reaction product of (a) a secondary amine and (b) diisopropenyl benzene, initiates polymerization to produce a polymer containing tertiary amine functional sites incorporated at the head of the polymer chain. A subclass of these polymers can be compounded to exhibit reduced hysteresis over conventionally prepared polymers.Type: GrantFiled: July 18, 1994Date of Patent: October 22, 1996Assignee: Bridgestone CorporationInventors: James E. Hall, David F. Lawson, Thomas A. Antkowiak
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Patent number: 5536801Abstract: An anionic polymerization initiator includes the C-lithio reaction product of an organolithium compound and a tertiary-amino allyllithium or a tertiary-amino xylyllithium. When used in an anionic polymerization, a functional group from the initiator is incorporated onto the head of the growing polymer and a lithium atom is incorporated at the "living" end of the polymer chain prior to quenching. The initiator may be used to polymerize a monomer(s) including diolefin monomers, monovinyl aromatic monomers and trienes, and the living ends of the polymers are effectively maintained even at temperatures of up to 300.degree. F. and higher. Such polymers exhibit an increased efficiency in coupling termination reactions, and products prepared from such polymers exhibit improved hysteresis characteristics. Products such as tires and the like can be prepared from such polymers and from vulcanizable elastomer compositions employing the polymers.Type: GrantFiled: June 6, 1995Date of Patent: July 16, 1996Assignee: Bridgestone CorporationInventors: Thomas A. Antkowiak, James E. Hall, David F. Lawson, John R. Schreffler, Mark L. Stayer, Jr.
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Patent number: 5523371Abstract: 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.Type: GrantFiled: April 7, 1995Date of Patent: June 4, 1996Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, Mark L. Stayer, Jr., John R. Schreffler, Hideki Komatsu
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Patent number: 5521309Abstract: An anionic polymerization initiator includes the C-lithio reaction product of an organolithium compound and a tertiary-amino allyllithium or a tertiary-amino xylyllithium. When used in an anionic polymerization, a functional group from the initiator is incorporated onto the head of the growing polymer and a lithium atom is incorporated at the "living" end of the polymer chain prior to quenching. The initiator may be used to polymerize a monomer(s) including diolefin monomers, monovinyl aromatic monomers and trienes, and the living ends of the polymers are effectively maintained even at temperatures of up to 300.degree. F. and higher. Such polymers exhibit an increased efficiency in coupling termination reactions, and products prepared from such polymers exhibit improved hysteresis characteristics. Products such as tires and the like can be prepared from such polymers and from vulcanizable elastomer compositions employing the polymers.Type: GrantFiled: December 23, 1994Date of Patent: May 28, 1996Assignee: Bridgestone CorporationInventors: Thomas A. Antkowiak, James E. Hall, David F. Lawson, John R. Schreffler, Mark L. Stayer, Jr.
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Patent number: 5519086Abstract: 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.Type: GrantFiled: April 7, 1995Date of Patent: May 21, 1996Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, Mark L. Stayer, Jr., John R. Schreffler, Hideki Komatsu
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Patent number: 5502131Abstract: An anionic polymerization initiator includes the C-lithio reaction product of an organolithium compound and a tertiary-amino allyllithium or a tertiary-amino xylyllithium. When used in an anionic polymerization, a functional group from the initiator is incorporated onto the head of the growing polymer and a lithium atom is incorporated at the "living" end of the polymer chain prior to quenching. The initiator may be used to polymerize a monomer(s) including diolefin monomers, monovinyl aromatic monomers and trienes, and the living ends of the polymers are effectively maintained even at temperatures of up to 300.degree. F. and higher. Such polymers exhibit an increased efficiency in coupling termination reactions, and products prepared from such polymers exhibit improved hysteresis characteristics. Products such as tires and the like can be prepared from such polymers and from vulcanizable elastomer compositions employing the polymers.Type: GrantFiled: June 6, 1995Date of Patent: March 26, 1996Assignee: Bridgestone CorporationInventors: Thomas A. Antkowiak, James E. Hall, David F. Lawson, John R. Schreffler, Mark L. Stayer, Jr.
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Patent number: 5502130Abstract: An anionic polymerization initiator includes a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A method of preparing an anionic polymerization initiator includes reacting an excess of a cyclic secondary amine with a conjugated diene to form an adduct; and, reacting the adduct with an organolithium compound. A method of preparing a polymer includes forming a solution of one or more anionically polymerizable monomers in a hydrocarbon solvent; and, polymerizing the monomer with an anionic polymerization initiator comprising a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A functionalized polymer includes the termination product of a living polymer having the general formula AYLi, Wherein A is a functional group derived from an anionic polymerization initiator; and, Y is a divalent polymer radical; wherein the anionic polymerization initiator is a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene.Type: GrantFiled: June 6, 1995Date of Patent: March 26, 1996Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr.
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Patent number: 5500447Abstract: An anionic polymerization initiator includes a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A method of preparing an anionic polymerization initiator includes reacting an excess of a cyclic secondary amine with a conjugated diene to form an adduct; and, reacting the adduct with an organolithium compound. A method of preparing a polymer includes forming a solution of one or more anionically polymerizable monomers in a hydrocarbon solvent; and, polymerizing the monomer with an anionic polymerization initiator comprising a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A functionalized polymer includes the termination product of a living polymer having the general formula AYLi, wherein A is a functional group derived from an anionic polymerization initiator; and, Y is a divalent polymer radical; wherein the anionic polymerization initiator is a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene.Type: GrantFiled: June 6, 1995Date of Patent: March 19, 1996Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr.
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Patent number: 5496940Abstract: An organolithium compound according to the present invention containing a cyclic amino group, has the general formula: ##STR1## wherein R.sub.1 is a divalent alkylene, an oxy- or amino-alkylene, or substituted alkylene having from 6 to about 20 carbon atoms; R.sub.2 is a linear-, branched-, or cyclo-alkylene having from about 2 to about 20 carbon atoms; and the lithium, Li, is bonded directly to a carbon atom of R.sub.2. A method of preparing an organolithium compound containing a cyclic amino group, comprising reacting a cyclic amino organo halide having the general formula ##STR2## where R.sub.1 and R.sub.2 are as above, and X is bromine or chlorine bonded directly to a carbon atom of R.sub.2, with a lithium reactant selected from lithium metal or an organolithium compound.Type: GrantFiled: February 1, 1995Date of Patent: March 5, 1996Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
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Patent number: 5491230Abstract: An anionic polymerization initiator includes a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A method of preparing an anionic polymerization initiator includes reacting an excess of a cyclic secondary amine with a conjugated diene to form an adduct; and, reacting the adduct with an organolithium compound. A method of preparing a polymer includes forming a solution of one or more anionically polymerizable monomers in a hydrocarbon solvent; and, polymerizing the monomer with an anionic polymerization initiator comprising a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene. A functionalized polymer includes the termination product of a living polymer having the general formula AYLi, wherein A is a functional group derived from an anionic polymerization initiator; and, Y is a divalent polymer radical; wherein the anionic polymerization initiator is a carbon-lithio salt of the adduct of a cyclic secondary amine with a conjugated diene.Type: GrantFiled: December 29, 1993Date of Patent: February 13, 1996Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr.
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Patent number: 5436290Abstract: 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.Type: GrantFiled: August 10, 1993Date of Patent: July 25, 1995Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, Mark L. Stayer, Jr., John R. Schreffler, Hideki Komatsu
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Patent number: 5420219Abstract: 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.Type: GrantFiled: August 10, 1993Date of Patent: May 30, 1995Assignee: Bridgestone CorportionInventors: David F. Lawson, Thomas A. Antkowiak, Mark L. Stayer, Jr., John R. Schreffler, Hideki Komatsu
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Patent number: 5354822Abstract: 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.Type: GrantFiled: September 8, 1992Date of Patent: October 11, 1994Assignee: Bridgestone/Firestone, Inc.Inventors: Thomas A. Antkowiak, David F. Lawson, Russell W. Koch, Mark L. Stayer, Jr.
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Patent number: 5334665Abstract: 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.Type: GrantFiled: May 6, 1993Date of Patent: August 2, 1994Assignee: Bridgestone/Firestone, Inc.Inventors: David F. Lawson, Mark L. Stayer, Jr., Thomas A. Antkowiak