Patents Represented by Attorney Robert A. Harman
  • Patent number: 4223001
    Abstract: An improved process is described for producing hydrogen from carbon monoxide and water in which carbon monoxide is contacted under homogeneous conditions with an alkaline aqueous liquid phase containing a soluble rhodium-containing catalyst at a reaction temperature from about 100.degree. to 300.degree. C. and at a reaction pressure from about 1 to 300 atmospheres in the presence of a saturated paraffinic water-soluble alcohol.
    Type: Grant
    Filed: June 20, 1978
    Date of Patent: September 16, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Miroslav Novotny, Lowell R. Anderson
  • Patent number: 4219635
    Abstract: Poly(ester/carbonates) are produced by adding phosgene to a reaction mixture of bisphenol A and terephthalic acid as ester-forming reactants, at mole ratios in the range between 2.0:0.8 and 2.0:1.3, in which the reaction medium consists essentially of pyridine, the concentration of bisphenol A plus terephthalic acid is in the range between 5 and 50 grams per 100 ml of pyridine; and the phosgene is added under agitation at a rate of at least 0.07 gm-mmole/liter.sec. The process is carried out at temperature in the range between 50.degree. C. and 115.degree. C. and not below the temperature given by the Arrhenius equation:1nU=10-12/0.001987 Twhere U is phosgene feed rate in gram-moles/liter.second and T is absolute temperature of the reaction mixture (degrees Kelvin). Preferred phosgene feed rates are at least 0.13 gram-millimoles/liter.second; and preferred temperatures of the reaction mixture are between 60.degree. C. and 80.degree. C.
    Type: Grant
    Filed: January 26, 1979
    Date of Patent: August 26, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Robert S. Cooke, Josefina T. Baker, Stylianos Sifniades
  • Patent number: 4219625
    Abstract: As an additive imparting oil and water repellency, durable against laundering and abrasion, to PET fibers: a partially or fully acylated polyol, especially pentaerythritol, glycerol, hydroquinone or ethylene glycol, acylated with a phthalic or terephthalic monoester having a perfluorinated alkyl or alkoxyalkyl C.sub.2 to C.sub.20 radical, especially C.sub.5 to C.sub.10 n-alkyl or (CF.sub.2).sub.n OR.sub.f where R.sub.f is C.sub.1 to C.sub.6 perfluoroalkyl, especially perfluoroisopropyl and (CF.sub.2).sub.n is a straight chain C.sub.2 to C.sub.10 diradical.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: August 26, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Frank Mares, Bryce C. Oxenrider, Cyril Woolf
  • Patent number: 4215208
    Abstract: Certain polyacetylenes exhibit reversible color changes at transition temperatures in the range -180.degree. to 220.degree. C., wherein the thermochromic cycles can be repeated many times with no apparent degradation and little change in spectroscopic properties.These thermochromic polyacetylenes are useful in temperature-indicator and indicia-display device applications.A process for laser-beam recording of images is described employing a thermochromic polyacetylene, in which the hysteresis properties of the polyacetylene can be suitably altered allowing for selectively storing or erasing the formed image.
    Type: Grant
    Filed: October 5, 1977
    Date of Patent: July 29, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Kwok C. Yee, Anthony F. Preziosi, Gordhanbhai N. Patel, Ronald R. Chance, Granville G. Miller, Ray H. Baughman
  • Patent number: 4215218
    Abstract: Direct reaction of anilines with olefins occurs at elevated temperature in solution containing dissolved complex of the aniline and an eighth group metal, especially rhodium. The products are N-alkylanilines and alkylquinolines.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: July 29, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Steven E. Diamond, Frank Mares
  • Patent number: 4208186
    Abstract: An improved process and device are described, for monitoring time-temperature histories of perishable articles, utilizing an inactive form of a diacetylene compound, incapable of undergoing a color change upon thermal annealing, but capable of conversion to an active form upon contacting an activating vapor. The active form is capable of undergoing a color change upon thermal annealing, as a result of solid state polymerization wherein the resulting color change is representative of the time-temperature history of thermal annealing. Specific active and inactive forms of diacetylenes useful in the improved process and device are also described.
    Type: Grant
    Filed: August 30, 1978
    Date of Patent: June 17, 1980
    Assignee: Allied Chemical Corporation
    Inventor: Gordhanbhai N. Patel
  • Patent number: 4208341
    Abstract: Muconic acid monoesters of alkanediols of 2-6 carbons and of phenol are prepared by copper (II) oxidative cleavage of phenols, catechols or orthobenzoquinones. The products are useful as comonomers in polyamides and other polymers. The alkanediol or phenol is introduced into the copper (II) reactant or catalyst.
    Type: Grant
    Filed: January 8, 1979
    Date of Patent: June 17, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Timothy R. Demmin, Milorad M. Rogic
  • Patent number: 4207305
    Abstract: A process of reacting in the liquid phase a hexacoordinated ruthenium(II) complex with oxygen in the presence of a source of hydrogen ions under conditions forming hydrogen peroxide and the corresponding hexacoordinated ruthenium(III) complex and reacting the hexacoordinated ruthenium(III) complex with hydrogen sulfide to form elemental sulfur and regenerate the hexacoordinated ruthenium(II) complex, the hexacoordinated ruthenium(III) complex having a reduction potential of not more than +0.68. Five or six of the ligands of the ruthenium complexes are non-labile in both valence states.
    Type: Grant
    Filed: April 27, 1979
    Date of Patent: June 10, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Steven E. Diamond, Frank Mares, Benjamin S. Tovrog
  • Patent number: 4206112
    Abstract: This invention describes novel ketals of .alpha.-oximinoketones, methods for the preparation of these compounds and includes novel intermediates formed during the production thereof. The novel class of compounds disclosed herein includes both .alpha.-oximinoketals, as well as the cyclic ketals of .alpha.-oximinoketones. This invention also discloses a novel class of .alpha.-nitrosoketal dimers produced during the synthesis of the corresponding .alpha.-oximinoketals, and it also discloses novel methods in the production thereof.
    Type: Grant
    Filed: December 13, 1978
    Date of Patent: June 3, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Milorad M. Rogic, Michael D. Swerdloff, Timothy R. Demmin
  • Patent number: 4202765
    Abstract: A process for separating hydroxylamine from an aqueous solution containing hydroxylammonium salts in mixture with salts of predominantly monovalent cations whose corresponding free bases have base dissociation constants greater than 10.sup.-7. Said solution is passed through a bed of cation exchange resin loaded predominantly with monovalent cations whereby hydroxylammonium and the other cations in solution substantially displace said cations from the resin. A second aqueous solution containing a monovalent amine or hydroxide base of at least 0.5 molar concentration having a dissociation constant greater than 10.sup.-7 is passed through the resin bed whereby hydroxylamine is preferentially released to the solution and the resin is correspondingly loaded with the cation of said base. Hydroxylammonium salts can be crystallized from the solution after addition of a stoichiometric amount of an appropriate acid.
    Type: Grant
    Filed: October 4, 1978
    Date of Patent: May 13, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Fred W. Koff, Allen A. Tunick, Stylianos Sifniades, Reed H. Belden
  • Patent number: 4200716
    Abstract: A process is described for polymerizing acetylene to selectively produce partially crystalline polyacetylene in its cis and trans configurations, which when doped with halogen additives, are useful as electrical conductors or semi-conductors. The polymerization is conducted in a solution containing a lithium dicyclopentadienyl titanium hydride catalyst in a liquid organic solvent therefor, at a temperature in the range of about -120.degree. to +250.degree. C. Lower process temperatures, such as below -60.degree. C., favor the formation of the cis form, and higher temperatures, above 0.degree. C., favor the formation of the trans form.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: April 29, 1980
    Assignee: Allied Chemical Corporation
    Inventor: Guido Pez
  • Patent number: 4195105
    Abstract: Fluorinated poly-(C.sub.2 to C.sub.10) alkylene polyamides (especially alpha, omega-triazaalkanes) in which the endmost nitrogen atoms are acylated by fluorinated carboxylic acid groups and an interior nitrogen atom is acylated by a dibasic acid moiety of the group consisting of (C.sub.4 to C.sub.14) alkane dioic acid moieties and the thiocarbonic acid moieties --C(.dbd.O)S-- and --CS.sub.2 --; wherein per the invention, a radical is terminally attached to the acylating dibasic acid moiety, of the group --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH(CH.sub.3)OH, --CH.sub.2 CH(OH)CH.sub.2 X (X being halogen or --CN), or ##STR1## The compounds are amphipathic, behaving like surfactants when incorporated with nylon. They are prepared by broadly known methods of producing esters and thioesters of acids. The stain resistance of fibers incorporating these compounds can be improved as to durability and at least partially restored after abrasion of the fiber, by annealing.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: March 25, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Frank Mares, Bryce C. Oxenrider, Cyril Woolf, deceased
  • Patent number: 4194038
    Abstract: A process for poly(ester-carbonates) from dihydric phenols, especially bisphenol A; aromatic or cycloaliphatic dicarboxylic acids, especially terephthalic acid; and phosgene as carbonate precursor wherein a reaction of the acid and phosgene is carried out in a first stage forming dicarboxylic acid chloride; and then phosgene and bisphenol A are added in separate streams, simultaneously during most of the second or condensation stage. Thereby only one kettle is required for carrying out the complete polymer production.
    Type: Grant
    Filed: January 25, 1979
    Date of Patent: March 18, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Josefina T. Baker, Robert S. Cooke, Stylianos Sifniades
  • Patent number: 4191696
    Abstract: A new liquid phase oxidation process in which a metal nitro complex transfers an oxygen atom from the nitro ligand to a substrate; especially such process conducted cyclically or catalytically using molecular oxygen as the oxygen source. Metal nitrosyl complex is formed as a coproduct together with an oxidation product of the substrate. In a catalytic process, molecular oxygen maintains a concentration of nitro ligand in the reaction mixture. In a cyclic process, nitrosyl ligand of the metal nitrosyl coproduct is reoxidized by molecular oxygen in presence of a monodentate base such as pyridine to nitro ligand; and the nitro complex, thus regenerated, can be used again to oxidize the substrate, In particular the metal is a Group VIII metal, especially cobalt and the nitro complex is pyridine cobalt nitro saloph. To accelerate oxidation of the substrate at given temperature, a cocatalyst is included in the reaction mixture, e.g.
    Type: Grant
    Filed: July 24, 1978
    Date of Patent: March 4, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Benjamin S. Tovrog, Steven E. Diamond, Frank Mares
  • Patent number: 4191790
    Abstract: Bisphenol-A/terephthalate/carbonate copolymer substrate in direct adhesive contact with a coating layer of polymerized allyl diglycol carbonate, ("ADGC") without substantial penetration of the copolymeric substrate by the coating layer. The coated article is prepared by forming a layer of monomeric ADGC on the substrate, then polymerizing the ADGC by free-radical initiation at temperatures maintained below successively higher limits as the polymerization progresses, whereby to avoid substantial penetration of the substrate by ADGC or its polymers. The resulting article, such as a clear sheet or plate, is abrasion resistant.
    Type: Grant
    Filed: August 8, 1978
    Date of Patent: March 4, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Daniel C. Chung, Dusan C. Prevorsek
  • Patent number: 4190595
    Abstract: A novel process is described for preparing low valent Group VIII metal hydrides, useful as catalysts in the hydrogenation of a large variety of organic compounds, in which a low valent Group VIII metal halide complex, such as (Ph.sub.3 P).sub.3 RhCl, is reacted with an alkali or alkaline earth metal alkylamide, such as LiN(CH.sub.3).sub.2, containing at least one alkyl group having an alkyl hydrogen atom in the beta position with respect to the metal atom. The metal alkylamide functions both as a dehalogenating and hydrogenating agent in the process. The process can be conducted at room temperature in a suitable organic solvent under an inert atmosphere utilizing the metal alkylamide in stoichiometric quantities. The process is also useful in preparing zero valent Group VIII metal complexes, such as (Ph.sub.3 P).sub.4 Pd.degree..
    Type: Grant
    Filed: August 8, 1978
    Date of Patent: February 26, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Steven E. Diamond, Frank Mares
  • Patent number: 4173708
    Abstract: A process is described for purifying 4,4'-benzophenonedicarboxylic acid, useful in preparing thermoplastic polyesters yielding molded articles having high impact strength, wherein the acid contains aromatic monocarboxylic acid genetic impurity, which comprises the steps of(a) mixing the impure 4,4-benzophenonedicarboxylic acid with aqueous ammonium hydroxide solution, containing about 28 weight percent or less of ammonia in a weight ratio of solution to acid of about 5:1 to 100:1, thereby forming a solution of the diammonium salt of the aromatic dicarboxylic acid;(b) mixing the resultant solution with an inert water-soluble organic liquid which is a non-solvent for the diammonium salt, in a weight ratio of organic liquid to solution not greater than about 20:1, thereby precipitating the diammonium salt of the acid;(c) separating the diammonium salt from the solution; and(d) recovering the aromatic dicarboxylic acid from the diammonium salt.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: November 6, 1979
    Assignee: Allied Chemical Corporation
    Inventors: Louis R. Palmer, James T. Karo
  • Patent number: 4171313
    Abstract: A catalytic system for oxidation of organic compounds including olefins, cyclic ketones and secondary alcohols. Soluble peroxo or solid supported oxo or peroxo complexes of molybdenum or tungsten are used in the presence of hydrogen peroxide to effect the oxidation. The resulting products include lactones, hydroxy acids, ketoacids, hydroxy esters and ketoesters from cyclic ketones; ketones from secondary alcohols and polyols or derivatives thereof from allylic alcohols.
    Type: Grant
    Filed: October 14, 1977
    Date of Patent: October 16, 1979
    Assignee: Allied Chemical Corporation
    Inventors: Frank Mares, Stephen E. Jacobson, Reginald T. Tang
  • Patent number: 4168297
    Abstract: An improved process is described for producing titanium dioxide from ilmenite-type ore. The ore is digested with aqueous hydrogen fluoride, the resulting liquid mixture treated with a water-soluble oxidizing agent, and the ferric iron impurities, in the resulting digestion solution, at a pH between about 1.0 and 6.0, are extracted out with a mono-or dialkyl, or mono- or di-(alkylphenyl) orthophosphoric acid, such as di-(2-ethylhexyl) orthophosphoric acid. The remaining solution is treated with ammonium hydroxide to precipitate hydrated titanium dioxide which is then calcined to form pigmentary titanium dioxide. Alkali metal and ammonium salts of the organophosphoric acid are also useful in the process.
    Type: Grant
    Filed: December 8, 1978
    Date of Patent: September 18, 1979
    Assignee: Allied Chemical Corporation
    Inventors: Krishnamurthy Nagasubramanian, Kang-Jen Liu
  • Patent number: 4166842
    Abstract: A process for obtaining hydroxylammonium salts from aqueous solutions containing hydroxylammonium salts in mixture with ammonium and/or sodium salts. Said solutions are contacted with a water immiscible organic solution containing a cation exchange compound of structure R.sub.1 COOX, or (R.sub.2 O)(R.sub.3 O)POOX, or (R.sub.2 O)PO(OX).sub.2, or mixtures thereof and optionally an additive of structure R.sub.4 R.sub.5 R.sub.6 PO, or (R.sub.4 O)(R.sub.5 O)(R.sub.6 O)PO, or mixtures thereof, wherein R.sub.1 is an alkyl or alkenyl group of from twelve to twenty carbon atoms, R.sub.2 and R.sub.3 are alkyl groups of from six to eighteen carbon atoms, R.sub.4, R.sub.5 and R.sub.6 are alkyl groups of from three to twelve carbon atoms, and X is H, Na or NH.sub.4, whereby hydroxylammonium ions are preferentially extracted from the aqueous phase in exchange for X from the organic phase.
    Type: Grant
    Filed: October 28, 1977
    Date of Patent: September 4, 1979
    Assignee: Allied Chemical Corporation
    Inventors: Allen A. Tunick, Fred W. Koff, Stylianos Sifniades