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).
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Patent number: 5739325Abstract: 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: GrantFiled: December 7, 1995Date of Patent: April 14, 1998Assignee: Thiokol CorporationInventors: Robert B. Wardle, W. Wayne Edwards
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Patent number: 5723604Abstract: 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: GrantFiled: June 22, 1995Date of Patent: March 3, 1998Assignee: Thiokol CorporationInventors: Louis F. Cannizzo, William W. Edwards, Robert B. Wardle, Thomas K. Highsmith
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Patent number: 5648556Abstract: 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: GrantFiled: November 14, 1994Date of Patent: July 15, 1997Assignee: Thiokol CorporationInventors: R. Scott Hamilton, Robert B. Wardle
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Patent number: 5587553Abstract: 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: GrantFiled: November 7, 1994Date of Patent: December 24, 1996Assignee: Thiokol CorporationInventors: Paul C. Braithwaite, Gary K. Lund, Robert B. Wardle
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Patent number: 5554820Abstract: 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: GrantFiled: March 20, 1995Date of Patent: September 10, 1996Assignee: Thiokol CorporationInventors: Robert B. Wardle, R. Scott Hamilton
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Patent number: 5529649Abstract: 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: GrantFiled: February 3, 1993Date of Patent: June 25, 1996Assignee: Thiokol CorporationInventors: Gary K. Lund, Tom K. Highsmith, Paul C. Braithwaite, Robert B. Wardle
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Patent number: 5516854Abstract: 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: GrantFiled: July 27, 1990Date of Patent: May 14, 1996Assignee: Thiokol CorporationInventors: Robert B. Wardle, W. Wayne Edwards, Jerald C. Hinshaw
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Patent number: 5498303Abstract: 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: GrantFiled: April 21, 1993Date of Patent: March 12, 1996Assignee: Thiokol CorporationInventors: Carol J. Hinshaw, Robert B. Wardle, Tom K. Highsmith
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Patent number: 5498711Abstract: 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: GrantFiled: August 2, 1993Date of Patent: March 12, 1996Assignee: Thiokol CorporationInventors: Thomas K. Highsmith, W. Wayne Edwards, Robert B. Wardle
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Patent number: 5472534Abstract: 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: GrantFiled: January 6, 1994Date of Patent: December 5, 1995Assignee: Thiokol CorporationInventors: Robert B. Wardle, Reed J. Blau
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Patent number: 5468866Abstract: 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: GrantFiled: January 4, 1994Date of Patent: November 21, 1995Assignee: Thiokol CorporationInventors: Thomas K. Highsmith, Robert M. Hajik, Robert B. Wardle, Gary K. Lund, Reed J. Blau
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Patent number: 5449835Abstract: 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: GrantFiled: November 14, 1994Date of Patent: September 12, 1995Assignee: Thiokol CorporationInventors: R. Scott Hamilton, Robert B. Wardle
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Patent number: 5366572Abstract: 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: GrantFiled: May 20, 1993Date of Patent: November 22, 1994Assignee: Thiokol CorporationInventors: R. Scott Hamilton, Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 5336343Abstract: 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: GrantFiled: April 16, 1993Date of Patent: August 9, 1994Assignee: Thiokol CorporationInventors: R. Scott Hamilton, Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 5292387Abstract: 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: GrantFiled: January 28, 1993Date of Patent: March 8, 1994Assignee: Thiokol CorporationInventors: Thomas K. Highsmith, Carol J. Hinshaw, Robert B. Wardle
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Patent number: 5099042Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.Type: GrantFiled: March 14, 1989Date of Patent: March 24, 1992Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 5015309Abstract: 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: GrantFiled: May 4, 1989Date of Patent: May 14, 1991Assignee: Morton International, Inc.Inventors: Robert B. Wardle, W. Wayne Edwards
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Patent number: 4988797Abstract: 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: GrantFiled: March 14, 1989Date of Patent: January 29, 1991Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 4952644Abstract: 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: GrantFiled: June 7, 1989Date of Patent: August 28, 1990Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw, William W. Edwards
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Patent number: 4931112Abstract: 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: GrantFiled: November 20, 1989Date of Patent: June 5, 1990Assignee: Morton International, Inc.Inventors: Robert B. Wardle, Jerald C. Hinshaw, Robert M. Hajik