Patents by Inventor Robert B. Wardle

Robert B. Wardle 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: 5739325
    Abstract: A process for the hydrogenolysis of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo?5.5.0.0.sup.5,9.0 .sup.3,11 !dodecane ("HBIW") is disclosed. In the process, a quantity of HBIW, a cosolvent, and a bromine source are placed into a reaction vessel. Acetic anhydride and a palladium hydrogenolysis catalyst are rapidly added to the reaction vessel. The hydrogenolysis catalyst should be substantially free of water. The reaction vessel is purged of an atmosphere capable of reacting with hydrogen, and hydrogen is quickly introduced into the reaction vessel to convert the HBIW to tetraacetyldibenzylhexaazaisowurtzitane ("TADB"). The acetic anhydride is added immediately prior to hydrogen introduction so that the acetic anhydride does not have time to react with the HBIW to form an acetylated derivative prior to commencement of the desired hydrogenation reaction. The process requires very little palladium catalyst, preferably less than 10% wt/wt based on the HBIW substrate.
    Type: Grant
    Filed: December 7, 1995
    Date of Patent: April 14, 1998
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, W. Wayne Edwards
  • Patent number: 5723604
    Abstract: A process of synthesizing HBIW using a mineral acid, such as perchloric acid, as the acid catalyst is disclosed. According to the process, glyoxal, adjusted to a pH from 4 to 7, and benzylamine are reacted in the presence of the mineral acid for sufficient time to form HBIW. The resulting HBIW is then isolated according to conventional separation techniques.
    Type: Grant
    Filed: June 22, 1995
    Date of Patent: March 3, 1998
    Assignee: Thiokol Corporation
    Inventors: Louis F. Cannizzo, William W. Edwards, Robert B. Wardle, Thomas K. Highsmith
  • Patent number: 5648556
    Abstract: A nonsolvent process of synthesizing bis(2,2-dinitropropyl)acetal (BDNPA) is disclosed. In the process, 2,2-dinitropropanol (DNPOH) is reacted at low temperature with an acetaldehyde source in the presence of an acid catalyst, such as a Lewis acid catalyst or protic acid catalyst. To inhibit by product formation, the reaction temperature is maintained from about -30.degree. C. to 30.degree. C. Upon completion of the reaction, the reaction solution is quenched with water and washed with an aqueous hydroxide solution. The hydroxide concentration should be sufficient to neutralize any acid formed during the quenching step and to solubilize unreacted 2,2-dinitropropanol as well as other aqueous soluble byproducts in the reaction solution. The BDNPA product is extracted with methyl tert-butyl ether (MTBE) or equivalent solvent. The organic solvent is evaporated to yield usable BDNPA product. The resulting yield is at least 50% based on the starting quantity of 2,2-dinitropropanol.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: July 15, 1997
    Assignee: Thiokol Corporation
    Inventors: R. Scott Hamilton, Robert B. Wardle
  • Patent number: 5587553
    Abstract: High solids pressable explosive compositions containing a liquid energetic polymer and a high performance explosive oxidizer are disclosed. The pressable explosive compositions contain a solids content between 91 and 99 weight percent, with an energetic polymer content less than 9 weight percent. The energetic polymer has a weight average molecular weight greater than 10,000, determined using a polystyrene standard, sufficient to use the polymer precipitation technique in preparing the pressable explosive compositions. Chain-extended PGN (polyglycidyl nitrate) is a preferred energetic polymer. The pressable explosives disclosed herein produce extremely high detonation pressure, high detonation velocity, and excellent metal accelerating capability.
    Type: Grant
    Filed: November 7, 1994
    Date of Patent: December 24, 1996
    Assignee: Thiokol Corporation
    Inventors: Paul C. Braithwaite, Gary K. Lund, Robert B. Wardle
  • Patent number: 5554820
    Abstract: A PBAN-based solid rocket motor propellant which includes more than 85% or more solids is provided. Propellants of this nature are possible using the combination of diepoxide curing agents and PBAN as a binder. The curing agents include diepoxides having 4 to about 10 carbon atoms. It has been observed that when a diepoxide curing agent is substituted for conventional curing agents, viscosities are significantly reduced, thus enabling the addition of higher percentages of solids in the propellant formulation. Total solids loading of over 85% are achievable while maintaining end-of-mix viscosities within acceptable ranges.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: September 10, 1996
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, R. Scott Hamilton
  • Patent number: 5529649
    Abstract: The use of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetrocyclo[5.5.0.0.sup.5,9 0.sup.3,11 ]-dodecane as the major explosive ingredient in compositions useful in high performance, low sensitivity explosive applications is disclosed.
    Type: Grant
    Filed: February 3, 1993
    Date of Patent: June 25, 1996
    Assignee: Thiokol Corporation
    Inventors: Gary K. Lund, Tom K. Highsmith, Paul C. Braithwaite, Robert B. Wardle
  • Patent number: 5516854
    Abstract: A method of preparing a thermoplastic elastomer having A blocks and at least one B block, wherein said A blocks are crystalline at temperatures below about 60.degree. C. and said B block is amorphous at temperatures above about -20.degree. C., said A blocks each being polyethers derived from monomers of oxetane and its derivatives and/or tetrahydrofuran and its derivatives, the method comprising:providing monofunctional hydroxyl terminated A blocks which are crystalline at temperatures below about 60.degree. C. and separately providing di-, tri- or tetrafunctional hydroxyl terminated B blocks which are amorphous at temperatures above about -20.degree. C.
    Type: Grant
    Filed: July 27, 1990
    Date of Patent: May 14, 1996
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, W. Wayne Edwards, Jerald C. Hinshaw
  • Patent number: 5498303
    Abstract: Composite propellant formulations are disclosed having a dinitramide salt oxidizer, such as ammonium dinitramide, an energetic binder, such as poly(glycidyl nitrate), a reactive metal, such as aluminum, and other typical propellant ingredients such as curatives and stabilizers. The disclosed propellant formulations are able to combust aluminum efficiently, possess high burn rates, and produce little or no HCl exhaust gases.
    Type: Grant
    Filed: April 21, 1993
    Date of Patent: March 12, 1996
    Assignee: Thiokol Corporation
    Inventors: Carol J. Hinshaw, Robert B. Wardle, Tom K. Highsmith
  • Patent number: 5498711
    Abstract: 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.0.sup.5,9 0.sup.3,11 ]dodecane is synthesized by reacting a diacyl-2,3,5,6-tetraoxypiperazine or tetraoxadiazaisowurtzitane derivative, a strong acid, and a nitrate source, such that an exothermic reaction occurs which proceeds at a temperature above ambient temperature. The reaction product is precipitated by cooling. It may be purified by washing with methanol and/or sodium bicarbonate and by simmering in nitric acid.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: March 12, 1996
    Assignee: Thiokol Corporation
    Inventors: Thomas K. Highsmith, W. Wayne Edwards, Robert B. Wardle
  • Patent number: 5472534
    Abstract: A composition is provided which comprises a fuel effective amount of a heterocyclic compound represented by the formula: ##STR1## wherein X is a non-metallic cation; and an oxidizing effective amount of an inorganic oxidizer. The oxidizer can be an inorganic nitrite, an inorganic nitrate, a metal peroxide, a metal oxide, a metal hydroxide, an inorganic perchlorate, or an inorganic chlorate. A binder can be added, if desired. An automotive air bag inflator and a method for generating gas are also disclosed.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: December 5, 1995
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Reed J. Blau
  • Patent number: 5468866
    Abstract: Methods of preparing bis-(1(2)H-tetrazol-5-yl)-amine (BTA) having improved physical and chemical characteristics are disclosed. In the process, a dicyanamide salt and an azide salt are reacted at high temperature in the presence of an acid reagent. Best yields are obtained when the reaction is allowed to proceed for approximately 48 hours. The dicyanamide salt is preferably present in a stoichiometric excess. The acid reagent has a pK.sub.a in the range from about 3 to about 9. The reaction mixture is acidified to a pH less than 3. Several variations of the acidification step permit control of particle size and morphology. Small, rounded particles are prepared by rapidly cooling the hot crude reaction product coincidentally with acidification. This is preferably accomplished by adding the hot crude reaction product directly to cold concentrated acid. The precipitated particles are isolated to yield BTA.
    Type: Grant
    Filed: January 4, 1994
    Date of Patent: November 21, 1995
    Assignee: Thiokol Corporation
    Inventors: Thomas K. Highsmith, Robert M. Hajik, Robert B. Wardle, Gary K. Lund, Reed J. Blau
  • Patent number: 5449835
    Abstract: A nonsolvent process of synthesizing bis(2,2-dinitropropyl)formal (BDNPF) is disclosed. In the process, 2,2-dinitropropanol (DNPOH) is reacted at low temperature with a formaldehyde source in the presence of a protic acid catalyst, such as H.sub.2 SO.sub.4, HCl, H.sub.3 PO.sub.4, or HBr. To inhibit byproduct formation, the reaction temperature is maintained from about -30.degree. C. to 30.degree. C. Upon completion of the reaction, the reaction solution is quenched with water and washed with an aqueous hydroxide ion solution. The hydroxide ion concentration should be sufficient to neutralize the protic acid catalyst during the quenching step and to solubilize unreacted 2,2-dinitropropanol as well as other aqueous soluble byproducts in the reaction solution. The BDNPF product is extracted with a low boiling temperature polar organic solvent, such as methyl tert-butyl ether (MTBE) or equivalent solvent. The organic solvent is evaporated to yield usable BDNPF product.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: September 12, 1995
    Assignee: Thiokol Corporation
    Inventors: R. Scott Hamilton, Robert B. Wardle
  • Patent number: 5366572
    Abstract: Oxazolines useful as bonding agents in solid rocket propellants are disclosed. The oxazoline bonding agents are capable of polymerizing in the presence of ammonium perchlorate. The bonding agents of the present invention are added to the propellant in a range from about 0.1% to about 3% concentration. Importantly, there is no increase in ammonia liberated above baseline propellant values and no increase in end of mix viscosities by using the oxazolines according to the present invention which provides substantial processing savings.
    Type: Grant
    Filed: May 20, 1993
    Date of Patent: November 22, 1994
    Assignee: Thiokol Corporation
    Inventors: R. Scott Hamilton, Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 5336343
    Abstract: Vinyl ethers for use as bonding agents in solid rocket propellants are disclosed. The vinyl ether bonding agents are capable of polymerizing in the presence of and around the surface of ammonium perchlorate particles. The bonding agents of the present invention are added to the propellant in a range from about 0.1% to about 3% by weight concentration. Importantly, there is no increase in ammonia liberated above baseline propellant values and no increase in end of mix viscosities by using the vinyl ethers according to the present invention which provides substantial processing savings.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: August 9, 1994
    Assignee: Thiokol Corporation
    Inventors: R. Scott Hamilton, Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 5292387
    Abstract: Ammonium nitrate is phase-stabilized against Phase IV.rarw..fwdarw.Phase III transition and the undesired volume changes associated with that phase change by including an effective amount of at least one metal dinitramide salt having the formula MX.sub.n wherein M is a metal cation, X is a dinitramide anion, and n is 1, 2 or 3. The phase-stabilized ammonium nitrate is useful in energetic applications such as solid propellants and explosives.
    Type: Grant
    Filed: January 28, 1993
    Date of Patent: March 8, 1994
    Assignee: Thiokol Corporation
    Inventors: Thomas K. Highsmith, Carol J. Hinshaw, Robert B. Wardle
  • Patent number: 5099042
    Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: March 24, 1992
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 5015309
    Abstract: Automotive airbag gas generant formulation providing alternative to commercially used formulations containing sodium azide. The composition comprises from about 25% to about 75% by weight of a heterocyclic compound having the following structure: ##STR1## wherein R is selected from hydrogen,--CO.sub.2 X, and--OXand X is a cation providing an anhydrous salt. The other principal ingredient of the composition is from about 25% to 75% by weight of an anhydrous oxidizing salt having a cation selected from metals of Group I-A of the Periodic Table (except sodium), calcium, strontium, or barium, and an anion which is essentially free of carbon, hydrogen, or halogens. From about 0% to 2% of a binder can be added, if necessary. An automotive airbag inflator containing the composition and a method for generating gas comprising the step of igniting the composition stated above are also disclosed.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: May 14, 1991
    Assignee: Morton International, Inc.
    Inventors: Robert B. Wardle, W. Wayne Edwards
  • Patent number: 4988797
    Abstract: Cyclic ethers having 4 and 5 member rings are polymerized with a alcohol initiator and an acid catalyst. The acid catalyst is used at a molar ratio relative to hydroxyl groups of the alcohol initiator of between about 0.05:1 and about 0.5:1.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: January 29, 1991
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 4952644
    Abstract: ABA triblock and A.sub.n B star polymers are produced by sequential cationic polymerization of 4 and 5 member ring cyclic ethers to initially form a B block and subsequent cationic polymerization of 4 and 5 member ring cyclic ethers to form A blocks at the termini of the B block. The B block is grown from the hydroxyl groups of a polyol having two or more hydroxyl groups, resulting in a B block having terminal hydroxyl functionality of two or greater. In growing each of the B and A blocks, the acid catalyst is used at a molar ratio relative to hydroxyl groups of the polyol initiator of between about 0.05:1 and about 0.5:1.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: August 28, 1990
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Jerald C. Hinshaw, William W. Edwards
  • Patent number: 4931112
    Abstract: Automotive airbag gas generant formulation providing an alternative to commercially used formulations containing sodium azide. The composition contains from about 25% to about 75% by weight of 5-nitro-1,2,4-trizal-3-one (usually known as nitrotriazolone). The other principal ingredient of the composition is from about 25% to about 75% by weight of an anhydrous oxidizing salt having a cation selected from metals of Group I-A of the Periodic Table (except sodium), calcium, strontium, or barium, and an anion which is essentially free of carbon, hydrogen, or halogens. From about 0.1% to about 5% of a binder can be added, if necessary. An automotive airbag inflator containing the composition and a method for generating gas comprising the step of igniting the composition stated above are also disclosed.
    Type: Grant
    Filed: November 20, 1989
    Date of Patent: June 5, 1990
    Assignee: Morton International, Inc.
    Inventors: Robert B. Wardle, Jerald C. Hinshaw, Robert M. Hajik