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).

  • Patent number: 5310798
    Abstract: 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.
    Type: Grant
    Filed: August 16, 1993
    Date of Patent: May 10, 1994
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: David F. Lawson, Mark L. Stayer, Jr., Thomas A. Antkowiak
  • Patent number: 5274106
    Abstract: 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: Grant
    Filed: December 30, 1991
    Date of Patent: December 28, 1993
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Thomas A. Antkowiak, Mark L. Stayer, Jr., John R. Schreffler, Hideki Komatsu
  • Patent number: 5268413
    Abstract: 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: Grant
    Filed: November 13, 1991
    Date of Patent: December 7, 1993
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: Thomas A. Antkowiak, David F. Lawson, Russell W. Koch, Mark L. Stayer, Jr.
  • Patent number: 5254628
    Abstract: 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.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: October 19, 1993
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Mark L. Stayer, Jr., Thomas A. Antkowiak
  • Patent number: 5227431
    Abstract: 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.
    Type: Grant
    Filed: April 12, 1991
    Date of Patent: July 13, 1993
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: David F. Lawson, Mark L. Stayer, Jr., Thomas A. Antkowiak, John R. Schreffler
  • Patent number: 5210144
    Abstract: 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.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: May 11, 1993
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Mark L. Stayer, Jr., Thomas A. Antkowiak
  • Patent number: 5210145
    Abstract: 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.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: May 11, 1993
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: David F. Lawson, Mark L. Stayer, Jr., Thomas A. Antkowiak
  • Patent number: 5153271
    Abstract: 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.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: October 6, 1992
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: David F. Lawson, Mark L. Stayer, Jr., Thomas A. Antkowiak
  • Patent number: 5153159
    Abstract: 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, fuctionalized polymers and vulcanizable elastomeric compounds having reduced hysteresis.
    Type: Grant
    Filed: April 9, 1990
    Date of Patent: October 6, 1992
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: Thomas A. Antkowiak, David F. Lawson, Russell W. Koch, Mark L. Stayer, Jr.
  • Patent number: 5109907
    Abstract: A process is provided for preparing a terminally functionalized polymer from a living polymer obtained by anionic polymerization of a diene monomer or mixture of a diene monomer and a vinyl aromatic hydrocarbon monomer which comprises reacting the living polymer with a compound 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 can be aryl groups.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: May 5, 1992
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: Mark L. Stayer, Jr., Thomas A. Antkowiak, David F. Lawson, Russell W. Koch
  • Patent number: 5066729
    Abstract: A process is provided for preparing a terminally functionalized polymer from a living polymer obtained by anionic polymerization of a diene monomer or mixture of a diene monomer and a vinyl aromatic hydrocarbon monomer which comprises reacting the living polymer with a compound 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 can be aryl groups.
    Type: Grant
    Filed: April 9, 1990
    Date of Patent: November 19, 1991
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: Mark L. Stayer, Jr., Thomas A. Antkowiak, David F. Lawson, Russell W. Koch
  • Patent number: 4357458
    Abstract: A process for preparing polyphosphazene polymers containing fluoroalkoxy and/or aryloxy substituents is provided. The process involves the reaction of a fluoroaliphatic alcohol or a substituted or unsubstituted aromatic alcohol or mixture of such alcohols with sodium hydroxide in an organic solvent or mixture of organic solvents which under appropriate conditions will form an azeotrope with water produced by the reaction. Water produced by the reaction is removed from the reaction mixture by azeotropic distillation thereby producing substantially dry sodium salts of said alcohols. The substantially dry sodium salts of the alcohols are then reacted with a linear polydichlorophosphazene polymer to produce polyphosphazene polymers containing fluoroalkoxy and/or aryloxy substituents.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: November 2, 1982
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Thomas A. Antkowiak, David J. Serbin
  • Patent number: 4258173
    Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is R(OR').sub.n O-- in which R is alkyl containing from 1 to 20 carbon atoms, aryl, alkylaryl or arylalkyl, R' is an alkylene radical and n is an integer from 1 to 70; wherein X' is X or is selected from the group consisting of substituted or unsubstituted alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups and wherein 20.ltoreq.(a+b+c).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form films and may also be utilized in applications for moldings, coatings, foams and the like.
    Type: Grant
    Filed: October 11, 1979
    Date of Patent: March 24, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Donald N. Schulz, Tai C. Cheng, Thomas A. Antkowiak
  • Patent number: 4137330
    Abstract: A process for producing benzene-soluble substantially linear dichlorophosphazene polymer having the formula (NPCl.sub.2).sub.x, in which x is greater than 20 and may be as high as 50,000 or higher, from a cyclic oligomer having the formula (NPCl.sub.2).sub.n, in which n is from 3 to 9, particularly the trimer (NPCl.sub.2).sub.3 or tetramer (NPCl.sub.2).sub.4, in the presence of a small but significant amount of an inorganic salt, preferably a halide of a metal such as Cr, Ni, Co, Cu, Fe, Mn or Mg which affords control of the molecular weight and avoids the formation of large amounts of gel.
    Type: Grant
    Filed: February 9, 1978
    Date of Patent: January 30, 1979
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Mark S. Prichard, Ashley S. Hilton, Mark L. Stayer, Jr., Thomas A. Antkowiak
  • Patent number: 3972841
    Abstract: The low temperature physical properties of copolymers and terpolymers containing fluoroalkoxy groups such as are described in U.S. Pat. Nos. 3,515,699 and 3,700,629 are improved by the incorporation of up to 35 mol % of non-fluorinated alkoxy groups in the polymers in place of some of the fluoroalkoxy groups. The polyphosphazenes of this invention also preferably contain a small amount of unsaturated substituent on the phosphazene backbone to enhance curability.
    Type: Grant
    Filed: January 29, 1975
    Date of Patent: August 3, 1976
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Tai Chun Cheng, Gary S. Kyker, Thomas A. Antkowiak