Patents Represented by Attorney Robert A. Harman
  • Patent number: 4440669
    Abstract: Electrically conducting doped poly(paraphenylene) compositions, and process of making such compositions, having direct current conductivities of at least 10.sup.-3 ohm.sup.-1 cm.sup.-1, at room temperature, and up to 100 ohm.sup.1 cm.sup.-1 and above; especially wherein the doping agent is a Group IA metal arene, a Group V halide, chlorine, bromine, or a mixture thereof; in particular potassium naphthalene, sodium naphthalene, AsF.sub.5, chlorine, or a mixture thereof. The polymers are useful as electronic devices, as substrates for electroplating, as materials for absorption of solar and of radio frequency radiation, and in general wherever electrical conductivity of the metallic type or of the semiconductor type, and light weight, are desired.
    Type: Grant
    Filed: February 17, 1981
    Date of Patent: April 3, 1984
    Assignee: Allied Corporation
    Inventors: Dawn M. Ivory, Granville G. Miller, Ronald R. Chance, Ray H. Baughman
  • Patent number: 4406825
    Abstract: Electrically conducting polyacetylene compositions are described having incorporated therein a fluorine-containing peroxide, such as FSO.sub.2 --O--O--SO.sub.2 F. Preferred compositions exhibit novel metal-like conductivity at temperatures above about 150.degree. K., and specific conductivities above about 10.sup.2 ohm.sup.-1 -cm.sup.-1 at room temperature, as measured by the standard four-probe method. A process for producing the compositions is also described in which polyacetylene is contacted with the peroxide, preferably in an inert liquid solvent at low temperatures.
    Type: Grant
    Filed: January 23, 1981
    Date of Patent: September 27, 1983
    Assignee: Allied Corporation
    Inventors: Guido Pez, Lowell R. Anderson
  • Patent number: 4402917
    Abstract: Uranium is extracted from phosphoric acid with organophosphorus extractants supported or impregnated on polymeric resins, and especially macroreticular resins. Suitable extractants include mono and dialkylphenyl esters of phosphoric acid. Uranium may be stripped from the supported or impregnated resins with hotter or more concentrated phosphoric acid, optionally with oxidation to hexavalent form, or with aqueous fluoride solutions.
    Type: Grant
    Filed: September 5, 1980
    Date of Patent: September 6, 1983
    Assignee: Allied Chemical Corporation
    Inventors: Theodore Largman, Stylianos Sifniades
  • Patent number: 4393233
    Abstract: The subject polymers are novel homopolymers and copolymers. The homopolymers are characterized by relatively high T.sub.g of about 120.degree. C. relative to their T.sub.m of about 250.degree. C., whereby they can readily be fabricated into fibers, films and like structures from the melt, and retain strength above 100.degree. C. The copolymers have T.sub.g 's intermediate between those of the homopolymers of the constituent monomers, and can be fabricated as for the subject homopolymers.Novel processes of obtaining the monomer, p-(1,1-dimethyl-2-hydroxyethyl)benzoic acid, are disclosed.
    Type: Grant
    Filed: January 7, 1982
    Date of Patent: July 12, 1983
    Assignee: Allied Corporation
    Inventors: Herbert K. Reimschuessel, Bruce T. DeBona
  • Patent number: 4392978
    Abstract: A method and reagent for the selective nitration of aromatic hydrocarbons which comprises contacting a complex of at least a catalytic amount of a polyether with a nitronium containing substance, e.g., NO.sub.2 BF.sub.4 with an aromatic hydrocarbon, e.g., toluene with at least one replaceable hydrogen. Nitration of toluene with these complexes at ambient temperature resulted in a reduction in meta substitution. In competitive studies, soluble crown ether complexes of NO.sub.2 BF.sub.4 in CH.sub.2 Cl.sub.2 nitrated toluene 45-59 times faster than they nitrated benzene.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: July 12, 1983
    Assignee: Allied Corporation
    Inventors: Ronald L. Elsenbaumer, Edel Wasserman
  • Patent number: 4362851
    Abstract: Crystalline adducts of the polyamides: poly-e-caproamide, poly(hexamethylene adipamide), poly-p-benzamide, poly(p-benzanilidene terephthalamide), and mixtures thereof; with the perfluorinated diacids: perfluorosuccinic acid, perfluoroglutaric acid, perfluoroadipic acid, and mixtures thereof. The polyamide components of the adducts contain at least 25 about amide groups in the polymer chain, preferably at least 75 amide groups for aliphatic polyamides and at least 50 amide groups for aromatic polyamides. The adducts can be formed into shaped objects from which diacid can be leached to produce a porous object useful for example as a filtration device.
    Type: Grant
    Filed: August 25, 1980
    Date of Patent: December 7, 1982
    Assignee: Allied Corporation
    Inventors: Shaul M. Aharoni, Edel Wasserman
  • Patent number: 4356138
    Abstract: Production of polyethylene filaments of tenacity at least 30 g/d from a hot, supersaturated solution of high viscosity polyethylene having intrinsic viscosity of at least 11 dl/g, by contacting a length of such filament (functioning as a seed) simultaneously with a stationary arcuate surface and with such polyethylene solution, and withdrawing the filament through the solution in sliding contact around the surface at a rate reaching at least 30 cm per minute thereby producing tension and inducing crystal growth from the solution onto the filament, with increase of tension up to a steady state tension of at least 70 grams. More particularly the polyethylene has intrinsic viscosity of 17-28 dl/g, the solvent is xylene, the surface is composed of PTFE, the polyethylene concentration is 0.1 to 0.5 wgt.
    Type: Grant
    Filed: January 15, 1981
    Date of Patent: October 26, 1982
    Assignee: Allied Corporation
    Inventors: Sheldon Kavesh, Dusan C. Prevorsek, Donald G. Wang
  • Patent number: 4326081
    Abstract: Hydrogenation of mononitroaromatic compounds, particularly nitrobenzene, nitrotoluene and their monochloro and monohydroxy ring substitution products, using hydrogen sulfide as reducing agent and a titanium dioxide catalyst at 200.degree.-400.degree. C. and atmospheric pressure.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: April 20, 1982
    Assignee: Allied Corporation
    Inventors: Charles T. Ratcliffe, Stuart L. Soled, Anthony J. Signorelli, Irving L. Mador
  • Patent number: 4310655
    Abstract: The subject polymers are novel homopolymers and copolymers. The homopolymers are characterized by relatively high T.sub.g of about 120.degree. C. relative to their T.sub.m of about 250.degree. C., whereby they can readily be fabricated into fibers, films and like structures from the melt, and retain strength above 100.degree. C. The copolymers have T.sub.g 's intermediate between those of the homopolymers of the constituent monomers, and can be fabricated as for the subject homopolymers.Novel processes of obtaining the monomer, p-(1,1-dimethyl-2-hydroxyethyl)benzoic acid, are disclosed.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Herbert K. Reimschuessel, Bruce T. DeBona
  • Patent number: 4310702
    Abstract: Sulfuryl chloride is reacted in the liquid phase with an organic reactant which is a ketone or aromatic alcohol unsubstituted on both ortho carbons in the presence of a moderator selected from the group consisting of aliphatic alcohols of 1-3 carbons and aliphatic ethers of 2-6 carbons, with sufficient moderator being present to selectively produce a product substantially free of compounds with more than one chlorine atom per carbonyl or aromatic hydroxy. The products, such as monochloroacetone, monochlorocyclohexanone, monochlorophenol and 2,2-bis(3-chloro-4-hydroxyphenyl)propane, are useful as chemical intermediates and as monomers for flame retardant polymers.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4289872
    Abstract: Formed from trifunctional units (M) having attached, to one of two terminal carbon atoms of an alkylene hydrocarbon diradical, the functional group A', and having attached, to the other terminal carbon atom, a different functional group B' reactive with A' to form a linkage AB; and having attached, to a third carbon of the skeleton of unit (M), the functional group A" (preferably the same as A') reactive with B' whereby a macromolecule is built up of successive layers of units (M). The process involves successive stages in the first of which, the functional groups A' are blocked and group B is blocked with a "source" unit (S); then groups A' are liberated to form Compound I. In the second stage, Compound II is formed from the starting material (such as lysine) by first blocking groups A', then converting group B' to a form reactive with A'.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: September 15, 1981
    Assignee: Allied Corporation
    Inventors: Robert G. Denkewalter, Jaroslav Kolc, William J. Lukasavage
  • Patent number: 4281194
    Abstract: An amorphous silica/alumina gel catalyst obtained by coprecipitating orthosilicate tetraester and aluminate triester in about 2.5:1 mole ratio, via rapid addition of about 0.4 to 5 moles of water per molecular equivalent of total ester groups, and drying at not over about 275.degree. C. is an effective catalyst for vapor phase reaction of cyclohexanone, ammonia and oxygen to form cyclohexanone oxime. This oxime can be rearranged to caprolactam, the starting material for nylon-6.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: July 28, 1981
    Assignee: Allied Chemical Corporation
    Inventors: John N. Armor, Emery J. Carlson
  • Patent number: 4276190
    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: July 26, 1979
    Date of Patent: June 30, 1981
    Assignee: Allied Chemical Corporation
    Inventor: Gordhanbhai N. Patel
  • Patent number: 4273947
    Abstract: A process is described for the heterogeneous hydrogenation of fluorine-containing alkyl, cycloalkyl, and benzene carboxylic acids to the corresponding primary alcohols. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture 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 acid 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: Grant
    Filed: January 31, 1979
    Date of Patent: June 16, 1981
    Assignee: Allied Chemical Corporation
    Inventor: Miroslav Novotny
  • Patent number: 4270864
    Abstract: A method and apparatus for spectroscopic material analysis are provided. Two coherent beams of monochromatic radiation are directed through a sample of material. A tuning mechanism adjusts the frequency difference between the radiation beams to equal substantially the rotational frequency of a preselected constituent of the material. Molecular energy of a preselected constituent of the material is increased, thereby producing a detectable signal in the form of a pressure wave. The signal is received by a detecting mechanism which indicates the magnitude thereof.
    Type: Grant
    Filed: March 14, 1979
    Date of Patent: June 2, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Joseph J. Barrett, Gary A. West
  • Patent number: 4269509
    Abstract: A method and apparatus for spectroscopic material analysis are provided. Two coherent beams of monochromatic radiation are directed through a sample of material. A tuning mechanism adjusts the frequency difference between the radiation beams to equal substantially the vibrational frequency of a preselected constituent of the material. Molecular energy of a preselected constituent of the material is increased, thereby producing a detectable signal in the form of a pressure wave. The signal is received by a detecting mechanism which indicates the magnitude thereof.
    Type: Grant
    Filed: May 2, 1979
    Date of Patent: May 26, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Michael J. Berry, Joseph J. Barrett
  • Patent number: 4269738
    Abstract: Electrically conducting polyacetylene compositions are described having incorporated therein a fluorine-containing peroxide, such as FSO.sub.2 --O--O--SO.sub.2 F. Preferred compositions exhibit novel metal-like conductivity at temperatures above about 150.degree. K., and specific conductivities above about 10.sup.2 ohm.sup.-1 -cm.sup.-1 at room temperature, as measured by the standard four-probe method. A process for producing the compositions is also described in which polyacetylene is contacted with the peroxide, preferably in an inert liquid solvent at low temperatures.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: May 26, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Guido Pez, Lowell R. Anderson
  • Patent number: 4268454
    Abstract: A novel class of compounds, anionic Group VIII metal hydrides containing phosphorus, arsenic and antimony organoligands is described, such as potassium tris and bis(triphenylphosphine) ruthenium hydride. The compounds are useful as homogeneous catalysts in the hydrogenation of aldehydes, ketones, olefins or alkynes. Processes for producing the compounds are also described.
    Type: Grant
    Filed: August 29, 1979
    Date of Patent: May 19, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Guido P. Pez, Roger A. Grey
  • Patent number: 4259527
    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: May 18, 1979
    Date of Patent: March 31, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Frank Mares, Stephen E. Jacobson, Reginald T. Tang
  • Patent number: 4259239
    Abstract: A racemic mixture of D- and L- forms of alpha-aminocaprolactam ("ACL") dissolved in e.g. ethanol is resolved, and preferably the undesired form remaining is solution is simultaneously racemized, by forming a supersaturated solution of the D,L-(ACL).sub.3 NiCl.sub.2. EtOH complex; providing an optically active form of lysine (e.g. L-lysine) as crystallization inhibitor of the undesired enantiomer of said complex (e.g. the D-form), and crystallizing a portion of the desired form of the complex from the solution. The undesired form remaining in solution can be simultaneously racemized by providing a strong base and an excess of ACL over the stoichiometric proportion required to form the complex. The recovered crystals of the desired form of the complex can be processed to afford the desired form of ACL, and to recover the nickel reagent. The ACL can be converted to the desired form of lysine, a nutritionally valuable amino acid.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: March 31, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Stylianos Sifniades, Meir Lahav, William J. Boyle, Jr.