Patents Represented by Attorney Robert A. Harman
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Patent number: 4255535Abstract: There are provided composites having near-zero uniaxial thermal expansion coefficients. One or more polyacetylenes having a negative uniaxial thermal expansion coefficient are uniaxially or biaxially oriented within one or more solid matrix materials having a positive thermal expansion coefficient to yield a composite material having a uniaxial thermal expansion coefficient which is nearly zero. The polyacetylenes are obtained by the solid-state polymerization of crystals of monomers containing at least one --C.tbd.C--C.tbd.C-- grouping per molecule. Also provided are processes for producing the above-described composites.Type: GrantFiled: December 15, 1978Date of Patent: March 10, 1981Assignee: Allied Chemical CorporationInventors: Ray H. Baughman, Edith A. Turi, Anthony F. Preziosi, Kwok-Chun Yee
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Patent number: 4255556Abstract: Poly(ester carbonate) polymers are prepared by reaction of bifunctional phenolates in an aqueous phase with phosgene and with the acyl halide of a bifunctional carboxylic acid halide such as terephthaloyl chloride in an organic solvent such as dichloromethane. At least a portion of the phosgene is reacted with the phenolate before or during reaction of the acid chloride with the phenolate to avoid the formation of polyester blocks which have limited solubility in the organic solvent. After reaction is complete, or at any stage wherein oligomers are formed, the aqueous phase can be cleanly removed and easily separated from the organic phase, and the organic phase readily washed free of by-products. The final polymer product is recovered from the washed organic phase and is colorless, substantially amorphous and melt processable, and has a high glass transition temperature.Type: GrantFiled: April 12, 1979Date of Patent: March 10, 1981Assignee: Allied Chemical CorporationInventors: Leon Segal, Bruce T. DeBona
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Patent number: 4255594Abstract: A process is described for the heterogeneous hydrogenation of haloalkyl, halocycloalkyl or haloaryl carboxylic anhydrides to the corresponding primary alcohols. In the haloalkyl or halocycloalkyl carboxylic anhydrides at least one halogen is in the alpha-position relative to the carboxylic anhydride grouping. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a supported or unsupported catalyst comprising a member of the group consisting of rhodium, iridium, metal oxides thereof, or mixtures thereof. In the liquid phase, the hydrogenation can be carried out batchwise under mild conditions of temperature and pressure, preferably at about 50.degree.-150.degree. C. and about 5-15 atmospheres, in an atmosphere containing hydrogen gas. A preferred embodiment is the hydrogenation of trifluoroacetic anhydride in the liquid phase to 2,2,2-trifluoroethanol, said alcohol being useful as an intermediate in the synthesis of the anesthetic, isoflurane, CF.sub.3 CHClOCHF.sub.2.Type: GrantFiled: September 18, 1979Date of Patent: March 10, 1981Assignee: Allied Chemical CorporationInventor: Miroslav Novotny
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Patent number: 4254059Abstract: A novel process is described for the homogeneous hydrogenation of nitriles to primary amines utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the high yield hydrogenation of nitriles to primary amines to be conducted under mild conditions of temperature and pressure with high selectivity and eliminates the need for the presence of ammonia to suppress the formation of significant amounts of secondary and tertiary amines.Type: GrantFiled: August 1, 1979Date of Patent: March 3, 1981Assignee: Allied Chemical CorporationInventors: Roger A. Grey, Guido P. Pez
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Patent number: 4252982Abstract: An anhydride of a carboxybenzene is esterified in solution by a fluorinated alcohol, using an aliphatic ester having a boiling point between about 50.degree. C. and about 150.degree. C. as solvent. In particular, pyromellitic dianhydride is esterified in an ester such as ethyl acetate or butyl acetate to the diester/diacid by reaction with 2-(n-perfluoroalkyl)ethanols having six to twelve carbon atoms in the perfluoroalkyl groups, and the reaction mixture containing the dissolved diester/diacid is admixed with an oxirane compound of the group ethylene oxide, epichlorohydrin and glycidol whereby the carboxyl groups are esterified in the solvent by reaction with oxirane groups. The product is recovered by evaporating off the solvent and unreacted oxirane compound. The product imparts oil and/or water repellency to textiles.Type: GrantFiled: October 29, 1979Date of Patent: February 24, 1981Assignee: Allied Chemical CorporationInventor: Bryce C. Oxenrider
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Patent number: 4240966Abstract: This invention describes novel cyclic ketals of .alpha.-oximinoketones and methods for the preparation of these compounds.Type: GrantFiled: December 13, 1978Date of Patent: December 23, 1980Assignee: Allied Chemical CorporationInventors: Milorad M. Rogic', Michael D. Swerdloff, Timothy R. Demmin
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Patent number: 4239929Abstract: Alkyl cyclohexa-1,3-dienes are aromatized with sulfur dioxide and oxygen. Cyclohexa-1,4-dienes are aromatized with sulfur dioxide. Conjugated dienic hydrocarbons, including alkyl cyclohexa-1,3-dienes, are converted to beta-olefinic peroxides by sulfur dioxide and oxygen. The aromatization reactions are useful as part of the synthesis of selected aromatics from acyclic olefins. The beta-olefinic peroxides are useful intermediates in the production of 1,4-diols.Type: GrantFiled: November 1, 1978Date of Patent: December 16, 1980Assignee: Allied Chemical CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4238352Abstract: A composition is described comprising at least two co-crystallized acetylenic compounds, of different chemical structures, each containing at least one --C.tbd.C-C.tbd.C-- group and substituents selected from the group consisting of sulfonate, urethane and alcohol radicals, at least one of the compounds capable of undergoing a contrasting color change upon exposure to actinic radiation or thermal annealing, wherein the composition exhibits a substantially different thermogram than the sum of thermograms of the individual components as obtained by differential scanning calorimetry.A device is also described useful for measuring the time-temperature or radiation-dosage history of an article comprising a substrate having deposited thereon the described composition.A process is also described for producing the composition of this invention.Type: GrantFiled: November 13, 1978Date of Patent: December 9, 1980Assignee: Allied Chemical CorporationInventor: Gordhanbhai N. Patel
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Patent number: 4235108Abstract: A composition is described comprising at least two co-crystallized acetylenic compounds, of different chemical structures, each containing at least one --C.tbd.C--C.tbd.C-- group and substituents selected from the group consisting of sulfonate, urethane and alcohol radicals, at least one of the compounds capable of undergoing a contrasting color change upon exposure to actinic radiation or thermal annealing, wherein the composition exhibits a substantially different thermogram than the sum of thermograms of the individual components as obtained by differential scanning calorimetry.A device is also described useful for measuring the time-temperature or radiation-dosage history of an article comprising a substrate having deposited thereon the described composition.A process is also described for producing the composition of this invention.Type: GrantFiled: November 13, 1978Date of Patent: November 25, 1980Assignee: Allied Chemical CorporationInventor: Gordhanbhai N. Patel
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Patent number: 4235699Abstract: Conversion of coal to products soluble in common solvents and conversion of coal tar to products of lower molecular weight, effected in liquid or fused reaction medium using a hydrogenating reactant, are carried out employing hydrogen sulfide and carbon monoxide as the sole or major hydrogenating reactant, without need of elemental hydrogen or a hydrogen donor solvent.Type: GrantFiled: March 5, 1979Date of Patent: November 25, 1980Assignee: Allied Chemical CorporationInventors: Charles T. Ratcliffe, Mahmoud B. Abdel-Baset
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Patent number: 4235453Abstract: One embodiment of this invention is a specially folded steering wheel safety bag adapted to be mounted in a steering column of a vehicle to cushion the driver. Another embodiment is a specially folded passenger safety bag adapted to be mounted in the dashboard or in another area of the vehicle to cushion a passenger. Both the steering wheel safety bag and the passenger safety bag include: a plurality of adjacent first-pleats; a plurality of between-first-pleat-folds; and a plurality of cross-pleat-folds. Each first-pleat has a first-pleat-fold. One such between-first-pleat-fold is disposed between adjacent first-pleats. The cross-pleat-folds are disposed substantially transverse to the first-pleats, the first-pleat-folds and the between-first-pleat-folds. The steering wheel safety bag may have from six to twenty such first-pleats and from one to four such cross-pleat-folds.Type: GrantFiled: May 13, 1974Date of Patent: November 25, 1980Assignee: Allied Chemical CorporationInventors: Lawrence C. Lawson, Richard L. Cascadden, Tsuneyo Ross, Patrick T. Greene
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Patent number: 4232951Abstract: Mesomorphic polyisocyanate compositions are described having extended rigid polymer backbones with flexible pendant groups. The compositions exhibit liquid-crystalline behavior and are useful in a device and process for displaying indicia, performing memory functions or indicating temperature. Novel polyisocyanate compositions for use in the above device and process are also described.Type: GrantFiled: August 4, 1978Date of Patent: November 11, 1980Assignee: Allied Chemical CorporationInventors: Shaul M. Aharoni, John P. Sibilia, Deborah R. Kozlowski
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Patent number: 4231948Abstract: Novel lithium dicyclopentadienyl titanium hydride type compositions are described, useful as catalysts in converting ethylene to 1-butene, which is used in producing "polymer gasoline" for increasing the octane number of automotive gasolines. Methods for synthesizing the novel compositions are also described.Type: GrantFiled: November 3, 1978Date of Patent: November 4, 1980Assignee: Allied Chemical CorporationInventor: Guido P. Pez
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Patent number: 4232170Abstract: A novel process is described for the homogeneous hydrogenation of carboxylic acid esters to primary alcohols utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the process to be conducted in solution under mild conditions of temperature and pressure with high selectivity and eliminates the disadvantages of utilizing heterogeneous catalysts. A process is also described for decarbonylating formate esters utilizing said compositions as catalysts.Type: GrantFiled: January 31, 1979Date of Patent: November 4, 1980Assignee: Allied Chemical CorporationInventors: Roger A. Grey, Guido P. Pez
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Patent number: 4228126Abstract: An improved recording device is described, useful for measuring the integrated time-temperature or integrated radiation-dosage history of an article, comprising a substrate onto which an acetylenic compound, containing at least two conjugated C.tbd.C groups, in an inactive form, is deposited. The inactive form is capable of being converted by melt or solvent recrystallization to an active form, which undergoes 1,4-addition polymerization resulting in an irreversible, progressive color change. The color change produced at any given point in time represents an integrated time-temperature history of thermal annealing or integrated radiation-dosage history of exposure to actinic radiation to which an article has been exposed.Also described is a process for producing an inactive form of the acetylenic compound. A film and a fiber, made from the inactive form of an acetylenic compound are also described.Type: GrantFiled: November 25, 1977Date of Patent: October 14, 1980Assignee: Allied Chemical CorporationInventors: Gordhanbhai N. Patel, Kwok C. Yee
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Patent number: 4228060Abstract: A process is described for producing partially crystalline polyacetylene in the cis or trans configurations utilizing.mu.-(.eta..sup.1 :.eta..sup.5 -cyclopentadienyl)-tris(.eta.-cyclopentadienyl)dititanium(Ti-Ti) catalyst. The resulting polyacetylene when "doped" with halogen additives is useful as an electrical conductor or semiconductor. Also described are polyacetylene "gels," consisting essentially of a solid polyacetylene and gel-forming liquid therefor, also containing up to about 10 percent by weight of catalyst, per weight of acetylene, which is used for production of the polyacetylene. The gels are stable to phase separation at room temperature in a closed system, and are useful in preparing randomly and partially chain-aligned polyacetylene films and articles.Type: GrantFiled: November 3, 1978Date of Patent: October 14, 1980Assignee: Allied Chemical CorporationInventor: Guido Pez
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Patent number: 4227028Abstract: A process for regioselective isomerization of organic compounds having a carbon-carbon double bond at a tertiary carbon atom by sulfur dioxide induced allylic rearrangement of a hydrogen atom and/or replacement of a proton in the allylic position by a deuteron. The organic compound is contacted with sulfur dioxide at temperatures between about 0.degree. and 70.degree. C. for a time sufficient to effect such isomerization to a more stable isomer; and if deuteration is to take place D.sub.2 O is provided in the solution.Type: GrantFiled: March 1, 1979Date of Patent: October 7, 1980Assignee: Allied Chemical CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4226812Abstract: An improved process is described for producing chlorotrifluoroethylene, a useful monomer for making high strength chlorofluoropolymers, comprising passing a mixture of 1,1,2-trichloro-1,2,2-trifluoroethane, ethylene, hydrogen chloride and elemental oxygen in the vapor phase, at a temperature from about 350.degree. to 525.degree. C., over a catalyst consisting essentially of a mixture of copper chloride and an alkali metal chloride, preferably a eutectic mixture, occluded in a molecular sieve, having an average pore size diameter in the range of about 5 to 11 angstroms.A new catalyst composition is also described, useful in oxyhydrochlorination processes conducted at temperatures above 350.degree. C., consisting essentially of a mixture of copper chloride and an alkali metal chloride, preferably a eutectic mixture, occluded in a molecular sieve, having an average pore size diameter in the range of about 5 to 11 angstroms.Type: GrantFiled: November 25, 1977Date of Patent: October 7, 1980Assignee: Allied Chemical CorporationInventors: Wim J. M. Pieters, William E. Gates, Franz Wenger
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Patent number: 4225511Abstract: Ammonia, oxygen e.g., as air, and a ketone react in contact with a gallium oxide catalyst at temperatures such as 50.degree.-500.degree. C., especially such catalyst obtained by heating hydrated gallium nitrate in air at about 350.degree. C. for several hours. The oximes have known utilities, including uses as oxidation inhibitors and as intermediates for production of amides. In particular, when the ketone is cyclohexanone, the cyclohexanone oxime in the reaction product can further be converted to the cyclic amide, caprolactam, e.g. by contacting the product with an aluminosilicate catalyst (treated with boric acid) having average pore diameter of at least 7 angstroms, especially a molecular sieve, suitably downstream in the same direction vessel. Caprolactam is the monomer starting material for nylon 6.Type: GrantFiled: April 16, 1979Date of Patent: September 30, 1980Assignee: Allied Chemical CorporationInventor: John N. Armor
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Patent number: 4224458Abstract: An improved process is described for the homogeneous hydrogenation of polycyclic aromatic hydrocarbons utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the process to be conducted under mild conditions of temperature and pressure with high selectivity for the production of partially hydrogenated derivatives of polycyclic aromatic hydrocarbons such as 1,2,3,4-tetrahydronaphthalene, and eliminates the need for the presence of base or carbon monoxide atmosphere in the process.Type: GrantFiled: January 31, 1979Date of Patent: September 23, 1980Assignee: Allied Chemical CorporationInventors: Roger A. Grey, Guido P. Pez