Patents Represented by Attorney Daniel N. Hall
  • Patent number: 5912343
    Abstract: A compound comprising at least one cyclic amine, having an organolithium side-chain, defined according to formula (I) ##STR1## wherein Z is a lithium atom (Li); R.sub.1 is selected from the group consisting of organic groups containing from 1 to about 12 carbon atoms and a bridging bond; each R.sub.2 is independently selected from the group consisting of hydrogen, organic groups containing from 1 to about 12 carbon atoms, and a bridging bond; each R.sub.3 is independently selected from the group consisting of hydrogen and organic groups containing from 1 to about 12 carbon atoms; a is an integer from 4 to about 16; and b is an integer from 0 to about 12; and optionally including a bridge, formed by the selection of two of said bridging bonds, the bridge having 0 to about 6 carbon atoms between the bridging ring members.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: June 15, 1999
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, William L. Hergenrother, Michael L. Kerns
  • Patent number: 5905116
    Abstract: The present invention teaches a method for enabling the formation of a high damping, soft polymer gel. The method includes: reacting a poly(.alpha.-olefin-co-maleimide) polymer with a maleated polyalkylene and an alkyl diamine under substantially dry conditions sufficient to form a polyalkylene grafted poly(.alpha.-olefin-co-maleimide) polymer product; and, dispersing the polyalkylene grafted poly(.alpha.-olefin-co-maleimide) polymer product with an extender oil sufficient to form the gel. The present invention also contemplates a polymer gel composition, a polymer composition and an article manufactured from the polymer gel composition.
    Type: Grant
    Filed: May 6, 1998
    Date of Patent: May 18, 1999
    Assignee: Bridgestone Corporation
    Inventors: Xiaorong Wang, Victor J. Foltz
  • Patent number: 5883183
    Abstract: The present invention is directed toward anionic polymerization employing lithio amines mixed with an organic alkali metal compound and optionally, a chelating reagent. The lithio amines have the general formula (A)Li(SOL)y, where SOL is a solubilizing component, A is an alkyl, dialkyl, cycloalkyl or dicycloalkyl amine radical or a cyclic amine, and y is 0 or is from about 0.5 to about 3. 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.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: March 16, 1999
    Assignee: Bridgestone Corporation
    Inventors: Takashi Kitamura, David F. Lawson, Koichi Morita, Yoichi Ozawa
  • Patent number: 5879484
    Abstract: A run flat pneumatic tire is reinforced by a thin annular composite band imbedded in the crown portion of the tire in combination with a plurality of radial cords or plies in its sidewalls which have freedom in shear with respect to one another. The band is formed by a plurality of layers of material strips wherein each strip is wound in a helical pattern, with adjacent strips being wound at reverse angles to each other. Each layer is formed under sufficient pressure and at an elevated temperature whereby the band is prestressed in tension which decreases the maximum stress at the footprint area of the tire. The invention furthermore incorporates the method of imparting the prestress on the annular band during its manufacture.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: March 9, 1999
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: Charles D. Spragg, Edward G. Markow, Thomas W. Bell
  • Patent number: 5877336
    Abstract: Triorgano substituted-tin lithium initiators are made in a dimethyl ether solvent. The substitution of dimethyl ether as the solvent for the traditional tetrahydrofuran solvent results in an initiator for anionic polymerizations that can produce less 1,2-vinyl repeat units. The dimethyl ether is also easier to remove from the polymerization media because it has a boiling point at one atmosphere of minus 24.8.degree. C. and thus is a gas at 25.degree. C.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: March 2, 1999
    Assignee: Bridgestone Corporation
    Inventors: William L. Hergenrother, Tristram W. Bethea
  • Patent number: 5877269
    Abstract: An organic ester suitable as a plasticizer is made from a glycol, a dicarboxylic acid, and an alcohol. The compound can be prepared in the presence of an organic solvent either by a one step route wherein the glycol, carboxylic acid, and alcohol are added together and reacted, or by a two step route wherein first the dicarboxylic acid is reacted with the glycol and the resulting acid ester is subsequently reacted with the alcohol. The end product is suitable as a plasticizer for rubbers such as neoprene wherein it has low volatility and imparts improved peel adhesion.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: March 2, 1999
    Assignee: Bridgestone Corporation
    Inventor: Russell W. Koch
  • Patent number: 5854327
    Abstract: A non-black roof sheeting material may be prepared from a composition of matter comprising 100 parts by weight of at least one polymeric rubber selected from the group consisting of ethylene-propylene-diene terpolymers, ethylene-propylene copolymers and other polyolefinic type polymers; from about 20 to about 300 parts by weight of a blend of at least two mineral fillers, per 100 parts of said polymeric rubber, wherein one of said mineral fillers is a reinforcing silica and wherein another of said mineral fillers is a chemically modified clay; from about 20 to about 150 parts by weight of a processing oil, per 100 parts of said polymeric rubber; from 1 to about 6 parts by weight of a sulfur cure package having at least one accelerator but being devoid of any thiuram accelerators, said cure package allowing said sheeting material to cure at about the same rate as a comparable black roof sheeting material at 160.degree. C.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: December 29, 1998
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: James A. Davis, Brian S. Alexander
  • Patent number: 5852189
    Abstract: Relatively pure tertiaryaminoalkyllithium initiators suitable for anionic polymerization reactions are prepared at low temperatures in an organic ether by reacting an equivalent excess of lithium metal with a tertiaryaminoalkylhalide. The lithium initiators are very stable at moderate temperatures when the ether is replaced by an aliphatic, a cycloaliphatic, or an aromatic solvent. Yields of the initiator in excess of 98% are readily achieved.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: December 22, 1998
    Assignee: Bridgestone Corporation
    Inventors: William L. Hergenrother, Michael L. Kerns, David F. Lawson
  • Patent number: 5792820
    Abstract: 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: Grant
    Filed: February 23, 1996
    Date of Patent: August 11, 1998
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
  • Patent number: 5785778
    Abstract: 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: Grant
    Filed: March 7, 1997
    Date of Patent: July 28, 1998
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
  • Patent number: 5786441
    Abstract: A functionalized polymer comprising a polymeric segment, having at least one cyclic amine end group, defined according to formula (I) ##STR1## where Z is an anionically-polymerized polymer; R.sub.1 is selected from the group consisting of organic groups containing from 1 to about 12 carbon atoms and a bridging bond; each R.sub.2 is independently selected from the group consisting of hydrogen, organic groups containing from 1 to about 12 carbon atoms, and a bridging bond; each R.sub.3 is independently selected from the group consisting of hydrogen and organic groups containing from 1 to about 12 carbon atoms; a is an integer from 4 to about 16; and b is an integer from 0 to about 12; and optionally including a bridge, formed by the selection of two of said bridging bonds, the bridge having 0 to about 6 carbon atoms between the bridging ring members; said polymer having been crosslinked. Also provided are vulcanizable compositions of matter, vulcanizates, and tires of the functionalized polymers.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: July 28, 1998
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, William L. Hergenrother, Michael L. Kerns
  • Patent number: 5736617
    Abstract: A method of terminating a living polymer comprising the step of reacting with a living polymer a terminator defined according to formula (I) ##STR1## where Z is a halogen atom; R.sub.1 is selected from the group consisting of organic groups containing from 1 to about 12 carbon atoms and a bridging bond; each R.sub.2 is independently selected from the group consisting of hydrogen, organic groups containing from 1 to about 12 carbon atoms, and a bridging bond; each R.sub.3 is independently selected from the group consisting of hydrogen and organic groups containing from 1 to about 12 carbon atoms; a is an integer from 4 to about 16; and b is an integer from 0 to about 12; and optionally including a bridge, formed by the selection of two of said bridging bonds, the bridge having 0 to about 6 carbon atoms between the bridging ring members. Also provided are a vulcanizable composition of matter, a vulcanizate and a tire comprising the functionalized polymers of the present invention.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: April 7, 1998
    Assignee: Bridgestone Corporation
    Inventors: Michael L. Kerns, William L. Hergenrother, David F. Lawson
  • Patent number: 5723533
    Abstract: An acyclic alkane soluble anionic polymerization initiator includes a mixture of from about 90 to about 10 parts by weight of a lithio amine having the general formula A.sub.1 Li and from about 10 to about 90 parts by weight of at least one other lithio amine having the general formula A.sub.2 Li. A.sub.1 and A.sub.2 are selected from the dialkyl, alkyl, cycloalkyl and dicycloalkyl amine radicals and cyclic amine radicals. There is also provided a method of forming a mixture of anionic polymerization initiators, a functionalized polymer and a method of forming a functionalized polymer.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 3, 1998
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, James E. Hall, Yoichi Ozawa
  • Patent number: 5700888
    Abstract: The present invention provides a method of anionic synthesis of stable macrocyclic polymers that are compounded to form vulcanizable elastomeric compounds exhibiting reduced hysteresis properties. Cyclic organometallic compounds containing divalent metal atoms of Groups IIA and IIB of the Periodic System are employed as initiators of anionic polymerization of conjugated diene, vinyl aromatic and/or triene monomers. Coupling of the living ends of the resulting macrocyclic polymers or copolymers with a coupling agent or a coupling agent that is also a functionalizing agent results in stable macrocyclic polymers with improved hysteresis properties.
    Type: Grant
    Filed: November 10, 1996
    Date of Patent: December 23, 1997
    Assignee: Bridgestone Corporation
    Inventor: James E. Hall
  • Patent number: 5698646
    Abstract: The present invention is directed toward anionic polymerization employing lithio aldimines mixed with an organic alkali metal compound and optionally, a chelating reagent. The lithio aldimines have the general formula (A)Li, where A is derived from a substituted aldimine. 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 a substituted aldimine and an organolithium compound. The resulting polymers may be modified with a terminating, coupling or linking agent, which may provide the polymer with a multifunctionality.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 16, 1997
    Assignee: Bridgestone Corporation
    Inventors: Takashi Kitamura, Mark L. Stayer, Jr., Akira Matsuda
  • Patent number: 5677399
    Abstract: The invention is a practical process for anionically synthesizing commercially significant quantities of macrocyclic polymers from polar and/or non-polar monomers by using Group IIA and IIB metal cyclic organometallic initiators. Activation of the ring metal atom results in anionic polymerization of the monomers by addition into the initiator ring at the bonds between the atom and its two adjacent carbon atoms, the metal atom acting as a bridge between the two living ends of the propagating chain. Coupling of the cyclic polymer living ends by coupling agents produces macrocyclic polymers that are stable in air and moisture and that exhibit desirable properties, such as low viscosities at high molecular weights. Such macrocyclic polymers provide enhanced polymer processability during molding, extruding and the forming of films.
    Type: Grant
    Filed: November 7, 1996
    Date of Patent: October 14, 1997
    Assignee: Bridgestone Corporation
    Inventor: James E. Hall
  • Patent number: 5674798
    Abstract: The invention is directed toward anionic polymerization employing lithio amines mixed with an organic alkali metal compound and optionally, a chelating reagent. The lithio amines have the general formula (A)Li(SOL).sub.y, where SOL is a solubilizing component, A is an alkyl, dialkyl, cycloalkyl or dicycloalkyl amine radical or a cyclic amine, and y is 0 or is from about 0.5 to about 3. 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.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: October 7, 1997
    Assignee: Bridgestone Corporation
    Inventors: Takashi Kitamura, David F. Lawson, Koichi Morita, Yoichi Ozawa
  • Patent number: 5645674
    Abstract: An improved method for achieving enhanced bond strength between components of unvulcanized and at least partially vulcanized rubber the improvement comprising the steps of selecting first and second initially unvulcanized rubber components (10, 12) for the manufacture of a vulcanized rubber article (21); applying an interphase layer (11) of rubber material, essentially devoid of crosslinking agents and containing from about 0.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: July 8, 1997
    Assignee: Bridgestone Corporation
    Inventors: Georg G. A. Bohm, James F. Cetnar
  • Patent number: 5643848
    Abstract: An acyclic alkane soluble anionic polymerization initiator includes a mixture of from about 90 to about 10 parts by weight of a lithio amine having the general formula A.sub.1 Li and from about 10 to about 90 parts by weight of at least one other lithio amine having the general formula A.sub.2 Li. A.sub.1 and A.sub.2 are selected from the dialkyl, alkyl, cycloalkyl and dicycloalkyl amine radicals and cyclic amine radicals. There is also provided a method of forming a mixture of anionic polymerization initiators, a functionalized polymer and a method of forming a functionalized polymer.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: July 1, 1997
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, James E. Hall, Yoichi Ozawa
  • Patent number: 5616704
    Abstract: 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 cyclic amine has an alkylene, oxy- or amino-alkylene group having from about 3 to about 16 methylene groups. 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.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: April 1, 1997
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Mark L. Stayer, Jr., David Saffles, H. James Harwood