Patents by Inventor Barton Milligan

Barton Milligan 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: 4885356
    Abstract: This invention relates to high molecular weight toluenediamine-containing polyamide resins formed by the reaction of a mixture of 2,4-toluenediamine and 2,6-toluenediamine and derivatives thereof with an aromatic diacid or precurser thereof. The resulting polyamides are amorphous, as opposed to crystalline. Because they are amorphous, they lend themselves to a wide variety of processing techniques and because of their high molecular weight, they have outstanding physical properties.The polyamides are prepared using a precondensate method wherein a mixture of the toluenediamine isomers and aromatic acid, usually in the form of the aromatic acid dihalide, is reacted at relatively low temperatures forming a precondensate and the precondensate subsequently polymerized in the presence of an acid acceptor.
    Type: Grant
    Filed: June 28, 1988
    Date of Patent: December 5, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, Roland Libers
  • Patent number: 4831146
    Abstract: This invention relates to an improved catalytic process for producing 2,2,6,6-tetraalkyl-4-oxopiperidines by the reaction of a ketone and ammonia. The improvement resides in using a catalytic amount of a super acid, i.e., a perfluorinated sulfonic acid polymer or perfluorinated alkyl sulfonic acid as the catalyst.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: May 16, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Denise B. Taylor, Barton Milligan
  • Patent number: 4816543
    Abstract: This invention relates to improved polyurethane systems prepared by reacting an organic polyisocyanate with a hydroxyl containing compound, the improvement comprising utilizing mono tertiary-alkyltoluenediamine where the tertiary-alkyl group is ortho to an amine group as a chain extender or component thereof. The ortho-tertiary-butyltoluenediamine isomer is particular effective for use in reaction injection molding of polyurethanes and can be formulated with polyol as a chain extender mix.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: March 28, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Jeremiah P. Casey, Dale D. Dixon, Barton Milligan
  • Patent number: 4810769
    Abstract: The present invention relates to polyurethanes and a method for making polyurethanes by reacting an organic diisocyanate, a glycol having a molecular weight of 500-5000 and a derivative of 2,6-diaminobenzoic acid or a blend comprising derivatives of 2,4-diaminobenzoic acid and 2,6-diaminobenzoic acid. The addition of the 2,6-diaminobenzoic acid derivative to the composition improves polyurethane processability and performance by decreasing chain extender reactivity and increasing hard segment regularity.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: March 7, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jeremiah P. Casey, Susan M. Clift, Barton Milligan
  • Patent number: 4786703
    Abstract: This invention relates to a polyisocyanate prepolymer for polyurethane/urea elastomer synthesis and to the resulting elastomer. The prepolymer is formed by reacting toluenediisocyanate with a long chain polyol under conditions such that essentially a 2:1 adduct is formed. Excess toluenediisocyanate is removed prior to forming the elastomer.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: November 22, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William E. Starner, Jeremiah P. Casey, Barton Milligan, Susan M. Clift
  • Patent number: 4745223
    Abstract: This invention relates to a class of tertiary-alkyltoluenediamines having alkyl groups ortho to an amine group. More particularly the aromatic diamines are represented by the formulas: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are C.sub.1-3 alkyl groups or R.sub.2 and R.sub.3 are combined to form a C.sub.5-6 membered ring.The above described alkylated aromatic diamines have been found to be well suited for use as a chain extender in forming polyurethane/urea elastomer systems and the mono tert-butyltoluenediamine isomers have been found to be nonmutagenic in the Ames test.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: May 17, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Jeremiah P. Casey, Dale D. Dixon, Barton Milligan
  • Patent number: 4724256
    Abstract: This invention relates to urethane linked hydroxy aromatic isocyanates and to a process for producing such urethane linked hydroxy aromatic isocyanates. The compositions are formed by reacting one equivalent aromatic diisocyanate with one equivalent of an alkylene polyol under conditions such that only one of the isocyanate groups react with the hydroxyl group of the polyol. Conditions are controlled such that the urethane linked hydroxy aromatic isocyanates are formed. The resulting product is suited for producing a variety of elastomers including a one component polyurethane elastomer.
    Type: Grant
    Filed: January 13, 1987
    Date of Patent: February 9, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William E. Starner, Barton Milligan, Roland E. Grandin
  • Patent number: 4722989
    Abstract: This invention relates to a solvent-free process for producing polyurethane/urea elastomers wherein an aromatic diisocyanate is reacted with a compound having active Zerewitinoff hydrogen atoms and an aromatic diamine chain extender. The improvement for producing urethanes having a wide range of properties comprises including a urethane-linked diisocyanate in the polyurethane urea elastomer. The urethane-linked diisocyanate is one that is formed by reacting toluenediisocyanate or substituent thereof with a short chain diol under conditions such that the urethane linked diisocyanate comprises two equivalents isocyanate per equivalent diol.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: February 2, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William E. Starner, Barton Milligan, Jeremiah P. Casey
  • Patent number: 4683279
    Abstract: This invention relates to urethane linked mixtures of 2,4- and 2,6-toluenediisocyanates (ULTDI dimers) having low melting points and to a method of forming these systems. The urethane linked toluenediisocyanates containing from 45-90% of the 2,4- and 10-55% of the 2,6- isomer by weight are formed by reacting two moles of an appropriate isomer mix of toluenediisocyanate, with one mole of a specific alkylene glycol, e.g., 1,2-butanediol, diethylene glycol or dipropylene glycol under conditions such that essentially only one of the isocyanate groups on a toluenediisocyanate molecule reacts with a hydroxyl group of the glycol. Conditions are controlled such that the urethane linked toluenediisocyanates are formed. The resulting product, which has two unreacted isocyanate groups, is suited for producing a variety of elastomers including polyurethane polyurethane/urea or polyurea elastomers.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: July 28, 1987
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, William E. Starner, Roland E. Grandin, Jeremiah P. Casey
  • Patent number: 4533765
    Abstract: This invention pertains to a process for preparing polyhydroxy aromatic compounds by reacting an alkali metal hydroxide with a hydroxymononuclear aromatic compound, e.g., phenol or resorcinol. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably nickel, or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The polyhydroxy aromatic compound is then formed by adding a protonating agent to the reaction product, with the protonating agent liberating the hydroxy compound from the salt.
    Type: Grant
    Filed: December 7, 1983
    Date of Patent: August 6, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, George B. DeLaMater
  • Patent number: 4533763
    Abstract: This invention pertains to a process for preparing hydroxy mononuclear aromatic compounds by reacting an alkali metal hydroxide with a mononuclear aromatic compound, e.g., benzene, xylene or toluene. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably copper, nickel, rhodium or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The hydroxy mononuclear aromatic compound is then formed by adding a protonating agent to the resulting reaction product, with the protonating agent liberating the hydroxy compound from the salt.
    Type: Grant
    Filed: December 14, 1983
    Date of Patent: August 6, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, George B. DeLaMater
  • Patent number: 4519432
    Abstract: This invention relates to reinforced tire utilizing polyurea or polyurethane formulations having low hysteresis. The polymer having low hysteresis is formed by reacting a prepolymer of an aromatic isocyanate and a high molecular weight difunctional polyol with a chain extender mix comprising an aromatic diamine and difunctional polyol. In these compositions the aromatic diisocyanate and aromatic diamine are selected so that there is substantial symmetry between the molecules. The reinforcement used is preferably an aromatic polyamide.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: May 28, 1985
    Assignee: Lim International S.A.
    Inventors: Andreas R. Schmidt, Herbert F. Strohmayer, Walter Sibral, Barton Milligan
  • Patent number: 4507459
    Abstract: This invention pertains to the synthesis of polyurethane systems having low hysteresis. The systems are generated by reacting a prepolymer of a mononuclear diisocyanate and a polyol with a chain extender mix of a mononuclear aromatic diamine and a polyol. The prepolymer should have a free isocyanate content of from 2 to about 12% by weight and the chain extender mix should have an amine to polyol equivalent from about 0.5 to 5:1.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: March 26, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Andreas R. Schmidt, Herbert F. Strohmayer, Walter Sibral, Barton Milligan
  • Patent number: 4501922
    Abstract: This invention pertains to a process for preparing mononuclear aromatic amines by reacting an alkali metal amide with a mononuclear aromatic compound, e.g., benzene and toluene. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably copper, nickel, rhodium or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The amine then is formed by adding a protonating agent to the resulting reaction product formed by the reaction of the alkali metal amide with the aromatic compound. The addition of the protonating agent liberates the amine.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: February 26, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Roland E. Grandin, Barton Milligan
  • Patent number: 4465876
    Abstract: In a process for nitrating aromatics using lower valent nitrating agents in trifluoroacetic acid, the product yield of nitroarenes can be significantly increased by maintaining an excess of nitrating agent over the stoichiometric amount during the reaction.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: August 14, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Barton Milligan
  • Patent number: 4448939
    Abstract: A composition for preparing polyurethanes comprising an organic polyisocyanate; a poly(silyldiamine) of the unit formula ##STR1## wherein the grouping ##STR2## is a divalent organic radical terminated by two nitrogen atoms with R being a divalent organic moiety, or a divalent alicyclic radical in which R and R.sup.1 with the two nitrogens form a cyclic diamine structure, R.sup.1 is hydrogen or a monovalent hydrocarbon, R.sup.2 is a monovalent hydrocarbon, and n is an integer greater than 1; and a polyol. When poly(silyldiamines) of the above formula are reacted with a polyisocyanate prepolymer and a polymeric polyol, elastomeric polyurethanes having good elastomeric properties are obtained.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: May 15, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael J. Fasolka, Barton Milligan
  • Patent number: 4341898
    Abstract: A process for the preparation of aromatic isocyanates from nitroalkanes. A nitromethyl aromatic compound of the general formula: ##STR1## wherein R and R.sub.1 represent hydrogen, halogen, a C.sub.1 -C.sub.5 alkyl radical, a C.sub.1 -C.sub.4 alkoxy radical, nitro, isocyanato, an alkoxycarbonylamino, or nitromethyl radical, with R and R.sub.1 being the same or different, is heated in the presence of an effective amount of a Lewis acid or Bronsted acid substance to effect a dehydrogenation-isomerization reaction to yield an aromatic isocyanate of the general formula: ##STR2## The product of the reaction may be recovered as the aromatic isocyanate or the alcohol adduct, a carbamate.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: July 27, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, Robert K. Pinschmidt, Jr.
  • Patent number: 4329501
    Abstract: The conversion of alkyl diaminobenzenes to the alkyl amino benzenes is carried out by contacting the alkyl diamino benzene with hydrogen in the presence of a nonsupported cobalt catalyst. Optionally, the reaction is carried out in the presence of water so that the water insoluble product formed can be separated from the water soluble reactants and by-products.
    Type: Grant
    Filed: October 9, 1980
    Date of Patent: May 11, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, Roland E. Grandin
  • Patent number: 4289908
    Abstract: This invention relates to an improvement in a process for preparing lower acyclic saturated amines by the gas phase hydrogenation of nitriles. To carry out the gas phase hydrogenation, the temperatures utilized in the reaction zone are from about 150.degree. to 350.degree. C., the pressure from about atmospheric to 500 psia, and the space velocity from about 750-20,000. Preferably, the conditions are controlled such that the components in the reaction zone are not exposed to a temperature greater than 380.degree. C. for a period of time in excess of 0.03 seconds.
    Type: Grant
    Filed: July 19, 1979
    Date of Patent: September 15, 1981
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Eckhart R. Becker, Randall J. Daughenbaugh, Barton Milligan
  • Patent number: 4257986
    Abstract: This invention relates to an improvement in a process for the manufacture of a nitroaromatic compound produced by the mixed sulfuric-nitric acid nitration method. The improvement resides in the refining of the aqueous acid mixture and comprises the following sequential steps: (a) contacting the mixed aqueous acid mixture, after nitration, with an oxidizing or a reducing agent under conditions effective for removing contaminant nitrous acid; (b) contacting the aqueous acid mixture in step (a) with feed aromatic compound to remove contaminant organics and residual nitric acid and then, if necessary, (c) contacting the remaining acid mixture with sufficient oxidizing agent under oxidizing conditions to remove residual organic components.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: March 24, 1981
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, Der-Shing Huang