Patents by Inventor Adel F. Halasa

Adel F. Halasa 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: 4997896
    Abstract: Trans-1,4-polybutadiene is a thermoplastic resin rather than a rubber at room temperature by virtue of its high degree of crystallinity. Because trans-1,4-polybutadiene contain many double bonds in its backbone, it can be blended and cocured with rubbers. It is accordingly an attractive alternative to conventional fillers such as carbon black, which are typically utilized in compounding rubber. By utilizing the catalyst system and techniques of this invention, trans-1,4-polybutadiene can be synthesized at a high level of conversion. This invention specifically relates to a process for the synthesis of trans-1,4-polybutadiene by an anionic polymerization process which comprises: (a) adding an alkali metal trialkylmagnesiate and an alkali metal alkoxide as a catalyst system to a polymerization medium containing 1,3-butadiene monomer and an organic solvent; and (b) allowing the 1,3-butadiene monomer to polymerize at a temperature which is within the range of about -10.degree. C. to about 50.degree. C.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: March 5, 1991
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Dennis B. Patterson, Adel F. Halasa
  • Patent number: 4935471
    Abstract: Polydiene rubbers are commonly compounded with carbon black in making a wide variety of rubber articles including tires, hoses and belts. It is generally desirable for the carbon black to be well dispersed throughout the polydiene in order to attain optimal physical properties. For instance, the traction and rolling resistance of tires which are made utilizing such rubbers can be improved by better dispersing the carbon black throughout the polydiene. The subject invention discloses a technique for capping polydienes in order to improve their affinity for carbon black. The present invention more specifially reveals a process for preparing a polydiene having a high level of affinity for carbon black which comprises reacting a metal terminated polydiene with a capping agent selected from the group consisting of (a) halogenated nitriles having the structural formula X--A--C.tbd.
    Type: Grant
    Filed: October 15, 1987
    Date of Patent: June 19, 1990
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel F. Halasa, Barry A. Matrana, Sylvia E. Robertson-Wilcox
  • Patent number: 4845165
    Abstract: Metals from Groups I and II and organometallic compounds thereof can be used to catalyze the polymerization of diene monomers into polymers. The polymers formed in such polymerizations are terminated with the metal used to catalyze the polymerization and are sometimes referred to as living polymers. Very useful blends of such polymers can be made by utilizing the process of the present invention.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: July 4, 1989
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel F. Halasa, Sylvia E. Robertson-Wilcox, David J. Zanzig, Richard J. Arconti, Wen L. Hsu
  • Patent number: 4843120
    Abstract: It has been determined that certain rubbery polymers having multiple glass transition temperatures can be utilized in making tires which have improved rolling resistance, improved wet skid resistance, and outstanding tread wear. These rubbery polymers are derived from at least one conjugated diolefin monomer, have a first glass transition temperature which is between -110.degree. C. and -20.degree. C. and have a second glass transition temperature which is between -50.degree. C. and 0.degree. C. These rubber polymers can be homopolymers of conjugated diolefin monomers, copolymers of more than one conjugated diolefin monomer, or copolymers derived from at least one conjugated diolefin monomer and at least one vinyl aromatic monomer.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: June 27, 1989
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel F. Halasa, Bill B. Gross, Joel L. Cox, George F. Balogh
  • Patent number: 4745145
    Abstract: Rubber compositions and articles such as tires having improved metal adhesion and metal adhesion retention to brass and brass-plated metallic reinforcement. The improvement comprises admixing from about 0.2 to about 6.0 parts per hundred rubber (phr) of a compound selected from the group consisting of 3-amino-2-carboxy-4-chlorobenzophenone, 3-hydroxy-2-methyldiphenylamine and 5-amino-2-methyl-N-phenylbenzensulfonamide and mixtures thereof with a vulcanizable rubber composition prior to embedding the metallic reinforcement therein and curing. A method for improving the metal adhesion and metal adhesion retention between a vulcanizable rubber and brass or brass-plated metallic reinforcement includes the step of dispersing from about 0.2 to about 6.0 phr of a compound selected from the group consisting of 3-amino-2-carboxy-4-chlorobenzophenone, 3-hydroxy-2-methyldiphenylamine and 5-amino-2-methyl-N-phenylbenzenesulfonamide and mixtures thereof in a vulcanizable rubber composition prior to curing.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: May 17, 1988
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Steven E. Schonfeld, Frederick J. Ravagnani, Adel F. Halasa
  • Patent number: 4730025
    Abstract: Metals from Groups I and II of the periodic table are commonly used to initiate the polymerization of conjugated diolefin monomers into polymers. The polymers formed in such polymerizations are terminated with the metal used to initiate the polymerization and are sometimes referred to as living polymers. Reactive end groups can be affixed to the chain ends of such polymers by utilizing the process of this invention. Such reactive end groups can subsequently be reacted with the backbone of other polymer chains. This results in the formation of a polymer having a reduced number of dangling chain ends. The functionalizing agents which can be utilized in the preparation of such polymers include hexachlorocyclopentadiene, tetraalkylthiuram disulfides, and chlorinated phenyl fulvenes.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: March 8, 1988
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Anthony J. Bell, Adel F. Halasa, Kenneth F. Castner, George F. Balogh
  • Patent number: 4696986
    Abstract: It has been determined that 1,2,3-trialkoxybenzenes and 1,2,4-trialkoxybenzenes can be utilized in order to increase the vinyl content of polydienes which are prepared utilizing lithium catalyst systems. For instance, it has been determined that 1,2,3-trimethoxybenzene and 1,2,4-trimethoxybenzene are very strong modifiers for utilization in such polymerizations. The utilization of the trialkoxybenzene modifiers of the present invention is highly advantageous because they promote fast polymerization rates and can be used to produce polymers having high vinyl contents.
    Type: Grant
    Filed: August 12, 1986
    Date of Patent: September 29, 1987
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel F. Halasa, Robert E. Cunningham
  • Patent number: 4623525
    Abstract: The present invention relates to the stabilization against water of solutions of poly(dichlorophosphazene) through the utilization of water reacting complexes of substituted silicon, tin, germanium or titanium chlorides which are complexed with a tertiary amine base.
    Type: Grant
    Filed: January 7, 1985
    Date of Patent: November 18, 1986
    Assignee: The Firestone Tire & Rubber Company
    Inventors: William L. Hergenrother, John W. Fieldhouse, Adel F. Halasa
  • Patent number: 4618650
    Abstract: Metals from groups I and II are commonly used to catalyze the polymerization of monomers into polymers. The polymers formed in such polymerizations are terminated with the metal used to catalyze the polymerization and are sometimes referred to as living polymers. Such polymers can be crosslinked to produce a polymeric network by utilizing the process of the present invention. More specifically, the present invention discloses a process for endlinking a living polymer comprising reacting the living polymer which is metal terminated with a halogenated silicon containing compound to produce a polymer which is terminated with halogenated silicon moieties; followed by reacting that polymer with a tertiary alcohol to produce a polymer which is terminated with hydroxy silyl moieties. The polymer which is terminated with hydroxy silyl moieties can then be endlinked into a network polymer that contains siloxane linkages by simply heating it.
    Type: Grant
    Filed: September 4, 1985
    Date of Patent: October 21, 1986
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel F. Halasa, George Jalics
  • Patent number: 4558103
    Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is --N(CH.sub.2 CHCH.sub.2).sub.2, and X' is a substituted or unsubstituted alkoxy, aryloxy, amino or mercapto substituent group or mixtures thereof which are compatible with diallylamino substituent and are known in the state of the art of polyphosphazene technology; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer and (y+z)>0.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams and the like.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: December 10, 1985
    Assignee: The Firestone Tire & Rubber Company
    Inventors: William L. Hergenrother, Adel F. Halasa
  • Patent number: 4431765
    Abstract: The invention herein is directed toward a process of preparing free flowing thermoset resin particles of polybutadiene and includes the steps of physically mixing a filler material with polybutadiene followed by chopping the mixture into small particles or granules which are irregularly shaped. A vulcanizing agent can be added during the mixing step as well as other ingredients commonly added to polybutadiene resin formulations, as is customarily done in the art, without affecting the free flowing properties of the polybutadiene treated according to the process of this invention.
    Type: Grant
    Filed: December 18, 1980
    Date of Patent: February 14, 1984
    Assignee: The Firestone Tire & Rubber Company
    Inventors: John M. Doshak, Mark R. Roodvoets, Adel F. Halasa
  • Patent number: 4291139
    Abstract: The process described herein involves the preparation of block copolymers of the S-B-S type wherein S represents a block of polystyrene and B represents a block of polybutadiene. In order to have the initial polystyrene block soluble in the polymerization medium, cyclohexane and aromatic hydrocarbons have been used as the diluent or solvent in these polymerizations. The present process permits the use of hexane as diluent by first preparing a "foot" or small block of homopolydiene to which the initial polystyrene block is thereafter attached. This small block of homopolydiene represents no more than 12 parts, preferably no more than 10 parts by weight of homopolydiene per 100 parts by weight of the block of polystyrene to which it is attached.
    Type: Grant
    Filed: March 9, 1977
    Date of Patent: September 22, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Adel F. Halasa, James E. Hall, Adolph Para
  • Patent number: 4268642
    Abstract: The terpolymers disclosed herein comprise 60-87 percent by weight butadiene, 10-30 percent styrene and 3-15 percent vinyl benzyl chloride in the polymer molecules. These are prepared by emulsion polymerization using a free radical generating initiator system. These terpolymers have excellent green strength and are useful in tire compositions.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: May 19, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Binnur Gunesin, Adel F. Halasa
  • Patent number: 4264753
    Abstract: The catalyst system disclosed herein comprises a combination or a chelate of a hydrocarbyl lithium compound with a bicyclic amine compound bridged together through nitrogen in each cyclic ring by means of 1-4, preferably 2-carbon atoms and each cyclic ring having at least one nitrogen and at least one other heteroatom in its cyclic structure selected from the class consisting of NR, O, S and PR. This catalyst system is particularly useful in the polymerization of vinyl compounds such as ethylene, propylene, styrene, butadiene, etc. The process for the polymerization of conjugated dienes produces polymers of excellent properties. For example, with butadiene-1,3 and other appropriate conditions, polybutadiene with high percentages of syndiotactic crystalline structure may be produced.
    Type: Grant
    Filed: May 20, 1980
    Date of Patent: April 28, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Adel F. Halasa, James E. Hali
  • Patent number: 4264759
    Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by: ##STR2## wherein R.sub.1, and R.sub.2 and R.sub.3 are independently selected from the group consisting of substituted or unsubstituted alkyl and alkoxy radicals containing from 1 to 12 carbon atoms and aryl radicals; X' is chlorine or a substituted or unsubstituted alkoxy, aryloxy, amino or mercapto radical or mixture thereof, which are compatible with the alkoxy substituent containing a fully substituted carbon in the beta position; and 20.ltoreq.(w+y+x).ltoreq. 50,000 per polymer.The polymers of the invention can be utilized to form protective films, and can also be utilized in applications such as for molding, coatings, foams and the like.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: April 28, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: William L. Hergenrother, Adel F. Halasa
  • Patent number: 4258160
    Abstract: 1,3-Butadiene is polymerized in the liquid phase in the presence of a catalyst composition comprising:(a) a cobalt-containing component;(b) R.sub.2 AlX wherein R is a hydrocarbon radical of 1-8 atoms, and X is halogen or hydrogen, and(c) COS.The cobalt-containing component may be a cobalt salt, such as a cobalt halide, carboxylate, thiocarboxylate, carbonate, thiocarbonate, etc. or a complex of such a salt with an oxygen-containing or nitrogen-containing group either in the same compound or in a separate compound. Typical aluminum compounds that may be used are dibutyl aluminum chloride, dipropyl aluminum chloride, diethyl aluminum chloride, bibutyl aluminum hydride, diamyl aluminum hydride, dipropyl aluminum hydride, etc. When the temperature for polymerization is maintained at -30.degree. to 30.degree. C., the resultant polymers have at least 40% syndiotactic-1,2 and with higher temperatures the syndiotactic-1,2 proportion increases until at 70.degree. C.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: March 24, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventor: Adel F. Halasa
  • Patent number: 4258171
    Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X and X' are the same or different and are represented by: ##STR2## wherein R.sub.1-4 are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, alkylmercapto, arylmercapto, dialkylamine, alkyl, aryl, alkoxy, aryloxy and heterocyclic radicals or R.sub.1 and R.sub.3 when taken together can form a cycloalkyl or heterocyclic ring; X' can also be selected from a group consisting of chloro radicals, substituted or unsubstituted alkoxy, aryloxy, amino and mercapto radicals or mixtures thereof; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams and the like.
    Type: Grant
    Filed: September 4, 1979
    Date of Patent: March 24, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: William L. Hergenrother, Adel F. Halasa
  • Patent number: 4258170
    Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by one or more of the following structural formulas: ##STR2## wherein R.sub.1-11 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, and substituted and unsubstituted alkyl, aryl, alkoxy, aryloxy, alkylmercapto, and dialkylamino radicals, and R.sub.1 or 3 and R.sub.2, or R.sub.5 and R.sub.6 taken together can form a substituted or unsubstituted benzene ring structure; X' can represent one or more substituents from the group consisting of a halogen radical, substituted and unsubstituted alkoxy, aryloxy, amino and mercapto radicals which are known in the state of the art in poly(phosphazene) technology and which are compatible with the copolymer substituents. The polymer can contain from 20 to 50,000 of such units such that 20.ltoreq.(w+y+z).ltoreq.50,000.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: March 24, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: William L. Hergenrother, Adel F. Halasa
  • Patent number: 4252914
    Abstract: Thermoplastic elastomer blends of alpha-olefin polymers and copolymers, such as polypropylene, having a melting point of at least 90.degree. C. with hydrogenated diblock copolymers of 1,4-polybutadiene and 1,2-polybutadiene have good physical properties such as low brittle point, good impact resistance at low temperatures, minimum creep at high temperatures, good elongation, good tensile and tear strengths and good impact strength. The blends can be repeatedly processed and still maintain good physical properties. The amount of alpha-olefin polymer or copolymer in the blend may range from about 10 percent to 60 percent, preferably 15 percent to about 48 percent with the amount of the hydrogenated butadiene block copolymer correspondingly ranging from about 90 percent to about 40 percent, preferably 85 percent to about 52 percent based on the combined weight of the two components. The blends are mixed at temperatures at least as high as the melting point of the alpha-olefin polymers or copolymer.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: February 24, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Adel F. Halasa, Davis W. Carlson, James E. Hall
  • Patent number: 4248988
    Abstract: The process described herein comprises the polymerization of a conjugated diene, such as butadiene-1,2, isoprene, etc., in an anhydrous hydrocarbon solution and in intimate contact with a catalyst system comprising a cobalt or nickel component, a hydrocarbyl aluminum compound and a halogenated hydrocarbon, such as CCl.sub.4, CH.sub.2 Cl.sub.2, CBr.sub.4, CHCl.sub.3, CHBr.sub.3, etc., containing 1-10 carbon atoms and 1-6 halogen atoms per molecule, with at least one of said halogen atoms being attached to an aliphatic carbon atom. Analysis shows that the polymer product has cyclic structure and this is confirmed by the determination of residual unsaturation which is found generally to be less than 20 percent of the normal unsaturation of the polymeric diene. The products are useful in molding compositions.
    Type: Grant
    Filed: October 18, 1979
    Date of Patent: February 3, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventor: Adel F. Halasa