Benzene Ring Bonded Directly To The Ring Nitrogen Of The Five-membered Hetero Patents (Class 548/476)
  • Patent number: 6352958
    Abstract: Novel herbicidal compounds, compositions containing them, and methods for their use in controlling weeds are disclosed. The novel herbicidal compounds are represented by formula I: where J is a 1-substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring attached at the 7 position of a benzofuran, benzoxazole, indole, 2,3-dihydrobenzimidazole or benzimidazole, and X is selected from hydrogen, halogen, cyano, nitro, and amino. Preferred R groups are optionally substituted alkyl groups.
    Type: Grant
    Filed: April 12, 2000
    Date of Patent: March 5, 2002
    Assignee: FMC Corporation
    Inventors: Scott D. Crawford, Lester L. Maravetz, George Theodoridis, Benjamin Dugan
  • Patent number: 6251829
    Abstract: This invention relates to herbicidal alpha-(2,4,5-trisubstituted)- and alpha-(2,5-disubstituted)-benzoyloxy-alpha-beta-, and/or beta-gamma-unsaturated-carboxylates and their derivatives, to compositions which contain these compounds, and to methods of use of these compounds.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: June 26, 2001
    Assignee: Rohm and Haas Company
    Inventors: Bin Li, Ying Man, Zongjian Zhang, Longhe Xu, Adam Chi-Tung Hsu
  • Patent number: 6124035
    Abstract: High temperature resins containing phenylethynyl groups that are processable by transfer molding have been prepared. These phenylethynyl containing oligomers were prepared from aromatic diamines containing phenylethynyl groups and various ratios of phthalic anhydride and 4-phenylethynlphthalic anhydride in glacial acetic acid to form a mixture of imide compounds in one step. This synthetic approach is advantageous since the products are a mixture of compounds and consequently exhibit a relatively low melting temperature. In addition, these materials exhibit low melt viscosities which are stable for several hours at 210-275.degree. C., and since the thermal reaction of the phenylethynyl group does not occur to any appreciable extent at temperatures below 300.degree. C., these materials have a broad processing window. Upon thermal cure at .about.300-350.degree. C., the phenylethynyl groups react to provide a crosslinked resin system.
    Type: Grant
    Filed: April 13, 1999
    Date of Patent: September 26, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: John W. Connell, Joseph G. Smith, Jr., Paul M. Hergenrother
  • Patent number: 6124484
    Abstract: The present invention provides a method for the preparation of triarylmethyl protecting group reagents. The reagents are prepared from reaction effluent from the cleavage step of oligonucleotide synthetic regimes.
    Type: Grant
    Filed: July 17, 1998
    Date of Patent: September 26, 2000
    Assignee: Isis Pharmaceuticals, Inc.
    Inventors: Yogesh S. Sanghvi, Zhiqiang Guo
  • Patent number: 6117822
    Abstract: Substituted phthalimidocinnamic acid derivatives I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl;R.sup.2 is H or halogen;R.sup.3 is CN, NO.sub.2, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -haloalkoxy;R.sup.4 is H, CN, NO.sub.2, halogen or C.sub.1 -C.sub.6 -alkyl;R.sup.5 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -hydroxyalkyl, C.sub.1 -C.sub.6 -mercaptoalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl;R.sup.6 is one of the radicals stated under R.sup.5 or CN, NO.sub.2, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy) carbonyl-C.sub.1 -C.sub.6 -alkyl, hydroxycarbonyl-C.sub.1 -C.sub.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: September 12, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Elisabeth Heistracher, Peter Plath, Christoph-Sweder von dem Bussche-Hunnefeld, Gerhard Hamprecht, Ralf Klintz, Peter Schafer, Karl-Otto Westphalen, Helmut Walter, Matthias Gerber, Ulf Misslitz
  • Patent number: 6066743
    Abstract: A method for the solventless synthesis of a phthalimide or phthalimide mixture is provided comprising contacting at least one amine reactant and at least one anhydride reactant in a solventless environment at a first temperature sufficient to allow the reactants to at least partially condense; and increasing the temperature to a second temperature sufficient to melt the reaction mixture, thereby allowing the reaction to go essentially to completion and form the reaction product.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: May 23, 2000
    Assignee: General Electric Company
    Inventors: Robert Joseph Nick, Mark Erik Nelson, Joseph John Caringi, Drew Elliot Williams
  • Patent number: 5807807
    Abstract: Substituted phthalimidocinnamic acid derivatives I ##STR1## wherein the variables are as defined in the description are useful as herbicides and for the desiccation and/or defoliation of plants.
    Type: Grant
    Filed: September 12, 1997
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Elisabeth Heistracher, Peter Plath, Christoph-Sweder von dem Bussche-Hunnefeld, Gerhard Hamprecht, Ralf Klintz, Peter Schafer, Karl-Otto Westphalen, Helmut Walter, Matthias Gerber, Ulf Misslitz
  • Patent number: 5709947
    Abstract: A method for the preparation of a diaminobisimide compound of the formula (I) substantially free of oligomers: ##STR1## wherein Ar.sup.1 is an optionally substituted aromatic residue which provides for good conjugation between the nitrogen containing groups; andAr is an optionally substituted aromatic residue characterized in that at least two molar proportions of an aromatic diamine of the formula (II)H.sub.2 N--Ar.sup.1 --NH.sub.2 (II)wherein Ar.sup.1 is as defined above,are heated with one molar proportion of an aromatic tetracarboxylic acid of the formula (III) or the corresponding dianhydride,(HOOC).sub.2 Ar(COOH).sub.2 (III)wherein Ar is as defined above,optionally in the presence of a polar solvent and optionally including 0.1 to 2 molar proportions of a tertiary amine.The compounds of formula (I) are useful curing agents in epoxy resin formulations.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: January 20, 1998
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Jonathan Howard Hodgkin, Mervyn Benjamin Jackson, John West Loder
  • Patent number: 5707937
    Abstract: Substituted phthalimidocinnamic acid derivatives I ##STR1## wherein the variables are as defined in the description are useful as herbicides and for the desication and/or defoliation of plants.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: January 13, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Elisabeth Heistracher, Peter Plath, Christoph-Sweder von dem Bussche-Hunnefeld, Gerhard Hamprecht, Ralf Klintz, Peter Schafer, Karl-Otto Westphalen, Helmut Walter, Matthias Gerber, Ulf Misslitz
  • Patent number: 5703098
    Abstract: Imide/amide ethers and alcohols are inhibitors of cytokines including tumor necrosis factor .alpha. and can be used to combat cachexia, endotoxic shock, arthritis, asthma, and retrovirus replication. A typical embodiment is 3-Phthalimido-3-(3', 4'-dimethoxyphenyl)propan-1-ol.
    Type: Grant
    Filed: December 3, 1996
    Date of Patent: December 30, 1997
    Assignee: Celgene Corporation
    Inventors: George W. Muller, Mary Shire, David I. Stirling
  • Patent number: 5703242
    Abstract: Purification process of imido-alkancaboxylic acids from contaminants represented by acid-carboxylic, lactam or aminoacids and water comprising:A) Preparation of the imido-alkancarboxylic acid precursor by reaction of an anhydride a1) or the corresponding acids, with an aminoacid b1) with water; or a1) with a lactam b2) and water; at temperatures comprised between 100.degree. and 250.degree. C., under pressure of an inert gas from 1 to 30 bar, for reaction times from 2 to 20 hours; wherein the ratio by moles between a1/(b1 or b2)/water is comprised between 1/1.05-1.1/0.5-2.5; optional addition of water such that it is at least, of 2 moles for mole of a1);B) discharge of the precursor obtained in phase A) in a solvent immiscible with water;C) separation of the aqueous phases from the organic phase;D) recovery of the organic phase for the successive peroxidation reaction.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: December 30, 1997
    Assignee: Ausimont, S.p.A.
    Inventors: Claudio Cavallotti, Gilberto Nucida, Claudio Troglia
  • Patent number: 5703245
    Abstract: Process for reducing the content of water in imido-alkanpercarboxylic acids comprising heating a suspension of imido-alkanpercarboxylc acid in water up to the complete solid melting and subsequent separation of the organic phase from the aqueous phase and recovery of the organic phase containing the imido-alkanpercarboxylic acid.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: December 30, 1997
    Assignee: Ausimont, S.p.A.
    Inventors: Claudio Cavallotti, Gilberto Nucida, Claudio Troglia
  • Patent number: 5696056
    Abstract: This invention relates to a novel phthalimide compound represented by formula: ##STR1## and a herbicide containing the same as an active ingredient. The compound of the present invention exhibit powerful herbicidal actions while securing sufficient safety to several important crops and are therefore useful as a herbicide.
    Type: Grant
    Filed: January 27, 1997
    Date of Patent: December 9, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Bunji Natsume, Shigeru Suzuki, Noriko Minami, Osamu Ikeda
  • Patent number: 5693797
    Abstract: A process for the preparation of brominated phthalimides that involves mixing tetrabromophthalic anhydride, an organic acid, and an organic dispersing agent in water at approximately 110.degree. C. under 1 bar pressure is disclosed. An amine is added and the reaction mixture is stirred for six hours under approximately 5 bar pressure and heated at least to 120.degree. C. The reactant mass is washed in water and then methanol. The process decreases production time, increases whiteness and purity, and decreases yellowness and particle size of the resulting product.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: December 2, 1997
    Assignee: Unitex Chemical Corporation
    Inventor: James F. Day
  • Patent number: 5663336
    Abstract: A process for the synthesis of compounds of formula I ##STR1## wherein Ar.sub.1, Ar.sub.2, A.sub.1, A.sub.2, R and X are as defined in the description, exhibit valuable pharmaceutical properties and are effective especially against diseases responsive to the inhibition of protein kinases, for example tumors.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: September 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Uwe Trinks, Peter Traxler
  • Patent number: 5594089
    Abstract: Thermomechanical and thermo-oxidative stabilities in heterocycle or heterocycle sulfone resin composites are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: January 14, 1997
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowtiz, Clyde H. Sheppard
  • Patent number: 5554769
    Abstract: The solvent-resistance and thermal stability of polyamideimides of the general formulae: ##STR1## is improved by capping the amideimides with a crosslinking functionality (Y) containing a residue selected from the group of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl (either including hydroxyl or halo-substituents), halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --C(R).sub.2 --;R=hydrogen, lower alkyl, or phenyl;T=methallyl or allyl;Me=methyl;R.sub.2 =a trivalent organic radical; andR.sub.3 =a divalent organic radical.The amideimide oligomers may be linear or multidimensional, and can be processed into blends, prepregs, or composites. Methods of making these amideimides and intermediates useful in the syntheses are also described. One such intermediate has the general formula:Y.sub.i --CONH--R.sub.3 --NH.sub.2and is the focus of the present application.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: September 10, 1996
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5534533
    Abstract: Novel carboxylate derivatives exhibiting phospholipase A.sub.2 inhibitory activity are disclosed, Specifically, the following compounds of the formula and pharmaceutically acceptable salts thereof are disclosed: ##STR1## wherein A is hydroxy, amino, or lower alkylamino; R.sup.1 to R.sup.12 are independently hydrogen, methyl, methoxy, or hydroxy, provided that all of R.sup.1 to R.sup.12 are not hydrogen; G.sup.1 is a single bond, or a group of --(CH.sub.2).sub.x O(CH.sub.2).sub.y -- wherein x and y are independently 0-5; G.sup.2 is a single bond, oxygen, sulfur, carbonyl, etc.; G.sup.3 is alkyl, aryl, or a group of the formula: ##STR2## wherein R.sup.13 and R.sup.14 are independently hydrogen, alkyl, aryl, etc.; or R.sup.13 and R.sup.14 may be taken together with the adjacent nitrogen atom to form a heterocyclic group or a group of the formula: ##STR3## wherein Z is a carbon atom or a nitrogen atom, J, K, and L are independently hydrogen or aryl, etc.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: July 9, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Toshiyuki Kato, Yozo Hori
  • Patent number: 5491144
    Abstract: Compounds of formula I ##STR1## wherein Ar.sub.1, Ar.sub.2, A.sub.1, A.sub.2, R and X are as defined in the description, exhibit valuable pharmaceutical properties and are effective especially against diseases responsive to the inhibition of protein kinases, for example tumors. They are prepared in a manner known per se.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: February 13, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Uwe Trinks, Peter Traxler
  • Patent number: 5466663
    Abstract: There is disclosed a compound of the formula: ##STR1## wherein X is hydrogen or halogen; Y is halogen; Z is oxygen or sulfur; R.sup.1 is hydrogen or alkyl; and R.sup.2 is a group of the formula: ##STR2## wherein R.sup.3 and R.sup.4 are the same or different, and each is hydrogen, alkyl, cycloalkyl or benzyl, or the ends of R.sup.3 and R.sup.4 are connected together to be alkylene; or R.sup.2 is a group of the formula: ##STR3## wherein R.sup.5 and R.sup.6 are the same or different, and each is hydrogen or alkyl, or the ends of R.sup.5 and R.sup.6 are connected together to be alkylene, with the proviso that R.sup.2 is a group of the formula: ##STR4## when Z is oxygen, which is useful as a herbicide.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: November 14, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsunori Hiratsuka, Minoru Takano, Masayuki Enomoto, Satoru Kizawa, Kazuo Saitoh
  • Patent number: 5442086
    Abstract: Disclosed are certain poly-methine compounds having the formula ##STR1## wherein each R.sup.1 is independently selected from cyano; carboxy; alkenyloxycarbonyl; an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; an unsubstituted or substituted, carbocyclic or heterocyclic aryl radical; an unsubstituted or substituted alkanoyl, cycloalkanoyl or aroyl radical; an unsubstituted or substituted carbamoyl radical; or an unsubstituted or substituted alkylsulfonyl, cycloalkylsulfonyl or arylsulfonyl radical; each R.sup.2 is independently selected from cyano or an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; each A is independently selected from an unsubstituted or substituted 1,2-phenylene or 1,2-naphthylene radical; each Z is independently selected from --0-- or --S--; and L is an organic linking group bonded by non-oxo carbon atoms to each Z atom.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: August 15, 1995
    Assignee: Eastman Chemical Company
    Inventors: James J. Krutak, Max A. Weaver, Clarence A. Coates, Jr., Samuel D. Hilbert, Terry A. Oldfield, William W. Parham, Wayne P. Pruett
  • Patent number: 5359084
    Abstract: A method for preparing an aromatic ether bisimide is provided. The mixture obtained from reacting a substituted phthalimide with a metal salt of a hydroxy aromatic compound in a non-polar solvent is extracted with about 4% to about 6% by weight aqueous alkali hydroxide solution to remove the reaction's by-products and thus provide substantially pure aromatic ether bisimide. The method is particularly suitable for extracting aromatic ether bisimide by-products from a continuous process preparing aromatic ether bisimide.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: October 25, 1994
    Assignee: General Electric Company
    Inventors: Brent Dellacoletta, Roy R. Odle
  • Patent number: 5302725
    Abstract: Aryl triflate compounds can generate a strong acid when exposed to irradiation of radiation and can be used as an acid generator in a radiologically-acid-producing agent system and a radiosensitive composition.
    Type: Grant
    Filed: October 20, 1992
    Date of Patent: April 12, 1994
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Makoto Kaji, S. Peter Pappas
  • Patent number: 5302740
    Abstract: Disclosed are certain poly-methine compounds having the formula ##STR1## wherein each R.sup.1 is independently selected from cyano; carboxy; alkenyloxycarbonyl; an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; an unsubstituted or substituted, carbocyclic or heterocyclic aryl radical; an unsubstituted or substituted alkanoyl, cycloalkanoyl or aroyl radical; an unsubstituted or substituted carbamoyl radical; or an unsubstituted or substituted alkylsulfonyl, cycloalkylsulfonyl or arylsulfonyl radical; each R.sup.2 is independently selected from cyano or an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; each A is independently selected from an unsubstituted or substituted 1,2-phenylene or 1,2-naphthylene radical; each Z is independently selected from --O-- or --S--; and L is an organic linking group bonded by non-oxo carbon atoms to each Z atom.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: April 12, 1994
    Assignee: Eastman Kodak Company
    Inventors: James J. Krutak, Max A. Weaver, Clarence A. Coates, Jr., Samuel D. Hilbert, Terry A. Oldfield, William W. Parham, Wayne P. Pruett
  • Patent number: 5294738
    Abstract: A process for the selective hydrodefluorination of a tetrafluorophthalimide compound of the formula ##STR1## where X is 1 and R is a monovalent organo group; or X is 2 and R is a divalent organo group; comprises reacting (I) the tetrafluorophthalimide with zinc in an aqueous alkali metal hydroxide medium. The product may be hydrolyzed to form 3,4,6-trifluorophthalic acid.
    Type: Grant
    Filed: April 3, 1992
    Date of Patent: March 15, 1994
    Assignee: Occidental Chemical Corporation
    Inventors: Jeffrey S. Stults, Lawrence B. Fertel, William S. Derwin
  • Patent number: 5288694
    Abstract: The invention relates to new N-aryl-nitrogen heterocycles of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or halogen,R.sup.2 represents hydrogen or an in each case optionally substituted, straight-chain or branched radical from the series comprising alkyl, alkenyl or cycloalkyl andA represents one of the radicals or ##STR2## where R.sup.3 represents alkyl,R.sup.4 represents alkyl andR.sup.5 represents hydrogen or alkyl,a plurality of processes for their preparation, and their use as herbicides.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: February 22, 1994
    Assignee: Bayer Atkiengesellschaft
    Inventors: Otto Schallner, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt, Renate Vosswinkel
  • Patent number: 5274135
    Abstract: A process for preparing a 3- or 4-aminobenzocyclobutene comprises aminating a 3- or 4-halo- or sulfonyloxybenzocyclobutene reactant with an aminating agent by heating at a temperature from about 80.degree. C. to a temperature at which dimerization or oligomerization of a benzocyclobutene reactant or product is a significant side reaction, in the presence of a metal-containing catalyst, for a time sufficient to aminate the halo- or sulfonyloxybenzocyclobutene reactant. In another aspect, this invention relates to a process for making a 3- or 4-phthalimido- or maleimidobenzocyclobutene, comprising reacting a 3- or 4-halobenzocyclobutene reactant with a phthalimide or maleimide compound in the presence of a metal-containing catalyst. The resulting phthalimido- or maleimidobenzocyclobutene can be hydrolyzed to a 3- or 4-aminobenzocyclobutene.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: December 28, 1993
    Assignee: The Dow Chemical Company
    Inventors: Kenneth J. Bruza, Arnold E. Young, Kurt A. Bell
  • Patent number: 5264588
    Abstract: Disclosed is a method of preparing a chloro-N-phenylphthalimide. A solution is prepared of a chlorophthalic acid or anhydride and aniline in water as the only solvent and the solution is heated to produce the product. The preferred chlorophthalic acid is 3,4,6-trichlorophthalic acid.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: November 23, 1993
    Assignee: Occidental Chemical Corporation
    Inventor: Chandrasekhar Krishnan
  • Patent number: 5256686
    Abstract: The phenylalkan(en)oic acids of the formula: ##STR1## as defined in the specification, possess an antagonistic activity on leukotriene B.sub.4.
    Type: Grant
    Filed: July 29, 1992
    Date of Patent: October 26, 1993
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Mitoshi Konno, Takahiko Nakae, Nobuyuki Hamanaka
  • Patent number: 5220015
    Abstract: Polymeric flame retardants comprise halogenated aromatic compounds having acylamino functional groups which are chemically bonded to cyclic imide-containing or imide-forming polymers or copolymers. The polymeric flame retardants are prepared by the reaction of halogenated aromatics containing a reactive hydrazido group with some or all of the anhydride groups of an cyclic alpha, beta-unsaturated dicarboxylic acid anhydride polymer or copolymer to form pendant halogenated-aromatic-substituted imide or amic acid groups. In addition, polymeric flame retardants are used to render thermoplastic resins less flammable under conditions which promote combustion. Novel flame retardant hydrazides are disclosed.
    Type: Grant
    Filed: April 3, 1992
    Date of Patent: June 15, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventors: Ronald E. MacLeay, Terry N. Myers
  • Patent number: 5206381
    Abstract: Solventless ultraviolet (UV) radiation curable polyamideimides which are useful as coatings for substrates are disclosed. The UV curable solventless polyamideimides are prepared by grafting acrylate functionality on the polyamideimide backbone The polyamideimides of the invention may be a part of UV curable compositions.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: April 27, 1993
    Assignee: Westinghouse Electric Corp.
    Inventor: Wei-Fang A. Su
  • Patent number: 5198526
    Abstract: Linear or multidimensional, crosslinking, solvent resistant oxazole, thiazole, or imidazole (i.e., heterocycle) oligomers and blends of the crosslinking oligomers and noncrosslinking comparable polymers are described. The oligomers are prepared by reacting tetraamines, diaminodiols, or diaminothiols (i.e. four-functional compounds) with poly-carboxylic acid halides, and crosslinking phenylimide end cap monomers in a suitable solvent under an inert atmosphere.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: March 30, 1993
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5192799
    Abstract: Amine represented by the following formula (1), or their acid addition salts or their quaternary ammonium salts. ##STR1## The amines of formula (1) or their pharmaceutically acceptable acid addition salts or quaternary ammonium salts are useful for the treatment and prevention of heart diseases of animals, particularly arrhythima, myocardial infarction, angina pectoris and heart failure and psychoneurological diseases.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: March 9, 1993
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Ikuo Tomino, Masaharu Ishiguro, Takumi Kitahara, Keiichi Yokoyama, Noriaki Kihara, Joji Kamiya, Kanji Yoshihara, Masaaki Ishii, Akira Mizuchi, Kazutoshi Horikomi, Akira Awaya, Takuo Nakano
  • Patent number: 5151487
    Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resing with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1 or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --.comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: September 29, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5102905
    Abstract: The invention concerns heterocyclic nitromethane derivatives of the formula 1 as defined hereinafter (and their non-toxic salts) wherein the heterocyclic moiety Q is thienyl, benzothienyl or dibenzothienyl and may bear a wide variety of optional substituents, together with pharmaceutical compositions containing them. The nitromethane derivatives are inhibitors of the enzyme aldose reductase and are of value in the treatment of certain complications of diabetes and galactosemia.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: April 7, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey Morris, John Preston
  • Patent number: 5087701
    Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resins with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --,comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers.
    Type: Grant
    Filed: March 5, 1990
    Date of Patent: February 11, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5082905
    Abstract: Linear or multidimensional, crosslinking, solvent resistant oxazole, thiazole, or imidazole (i.e., heterocycle) oligomers and blends of the crosslinking oligomers and noncrosslinking comparable polymers are described. The oligomers are prepared by reacting tetraamines, diaminodiols, or diaminothiols (i.e. four-functional compounds) with poly-carboxylic acid halides, and crosslinking phenylimide end cap monomers in a suitable solvent under an inert atmosphere.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: January 21, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5071941
    Abstract: The solvent resistance of polyethersulfone oligomers is enhanced by using difunctional imidophenol end-cap monomers to provide improved crosslinking. The imidophenol monomers include two unsaturated functionalities capable of cross-linking upon thermal or chemical activation. Blends, pregregs, and composites using the novel end caps are described for linear or multidimensional polyethersulfone oligomers.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: December 10, 1991
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5070197
    Abstract: A method of preparing a water-soluble or water-dispersible pesticidal composition is described. The pesticidal composition is prepared in a continuous process by intimately mixing a Bronsted acid precursor of the pesticidally active compound with a Bronsted base under reaction conditions in an extruder. The reaction is performed with minimal solvent and under conditions where the water of reaction volatilizes during the course of the reaction.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: December 3, 1991
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: James Chin, James B. Marshall, Michael D. Drozdick, Fred C. Rosa, Frederick D. Judge
  • Patent number: 5047553
    Abstract: Chlorinated phthalic anhydrides are converted to fluorinated phthalic acids without dilactone formation by reacting an anhydride with a primary amine under anhydrous conditions to form the corresponding chlorinated-N-substituted phthalimide which in turn is reacted with a fluorinating agent under anhydrous conditions to form the corresponding fluorinated phthalimide which is hydrolyzed to form the corresponding fluorinated phthalic acid.In a preferred embodiment tetrachlorophthalic anhydride is refluxed with aniline in the presence of glacial acetic acid for 5 to 10 hours to form tetrachloro-N-phenylphthalimide which is reacted with KF in sulfolane in the presence of tributylhexadecylophosphonium bromide under nitrogen at 140.degree. C. to 160.degree. C. for 10 to 15 hours to form tetrafluoro-N-phenylphthalimide which in turn is hydrolyzed by refluxing with 50% H.sub.2 SO.sub.4 for 15 to 25 hours. The tetrafluoro-N-phenylphthalimide is a novel compound.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: September 10, 1991
    Assignee: Occidental Chemical Corporation
    Inventors: Deanne M. Nowak, Henry C. Lin
  • Patent number: 5024694
    Abstract: Herbicidal and plant growth-regulating N-aryl heterocycles of the formula ##STR1## where A represents one of the groupings ##STR2## where R.sup.1 and R.sup.2 in each case independently of one another represent hydrogen, halogen, halogenoalkyl or alkyl,Y.sup.1 and Y.sup.2 in each case represent oxygen or sulphur andZ represents hydrogen, hydroxyl or chlorine, R represents in each case optionally branched alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl or cycloalkenylalkyl in each case interrupted by at least one oxygen atom and in each case substituted by at least one fluorine atom,X represents hydrogen or halogen andY represents hydrogen or halogen.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: June 18, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Schallner, Michael Negele, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt, Birgit Krauskopf
  • Patent number: 5011905
    Abstract: Polyimide oligomers include (1) linear, monofunctional crosslinking oligomers prepared by condensing a monoanhydride end cap with a diamine that includes alternating ether and "sulfone" (--SO.sub.2 --, --S--, --CO--, --(CF.sub.3).sub.2 C--, or --(CH.sub.3).sub.2 C--) linkages connecting alternating aromatic radicals and with a dianhydride (or dianhydride mixture), particularly the unsaturated, aliphatic dianhydride commonly known as MCTC; (2) linear, mono- or difunctional crosslinking oligomers prepared by condensing an amine end cap with a diamine and a dianhydride; and (3) multidimensional, crosslinking oligomers having an aromatic hub and at least three radiating arms connected to the hub, each arm including a crosslinking end cap at its distal end and at least one imide linkage.Blends, prepregs, and composites can be prepared from the oligomers.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: April 30, 1991
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4990627
    Abstract: The polyetherimides have repeating groups which may be represented by the general formula: ##STR1## They are produced from novel monomers of the formula ##STR2## Synthesis procedures for forming such monomers are also described.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: February 5, 1991
    Assignee: Ethyl Corporation
    Inventors: Gene C. Robinson, G. Patrick Stahly
  • Patent number: 4985568
    Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resing with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --.comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers. The imidophenylamines are prepared by reacting the corresponding acid halide with ammonia to form an amic acid and rearranging the amic acid to the amine.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: January 15, 1991
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4980481
    Abstract: High performance composites can be made from linear or multidimensional oligomer or blends that include unsaturated hydrocarbon crosslinking functionalities linked to a pyrimidine radical on the terminal ends of the polymeric backbones of the oligomers. The oligomers are made by condensing pyrimidine-based end-cap monomers of the formula: ##STR1## wherein Z=--OH or halogen;Y= ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --O--, --S--, --SO--, --CO--, --CHR--, --CR.sub.2 --, or --SO.sub.2 --;T=methallyl or allyl;Me=methyl; andR=hydrogen, lower alkyl, or phenyl,with suitable polymeric precursors.
    Type: Grant
    Filed: March 14, 1988
    Date of Patent: December 25, 1990
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4978787
    Abstract: A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group or a C.sub.3 -C.sub.7 cycloalkyl group, which is useful as a herbicide.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: December 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
  • Patent number: 4965336
    Abstract: Linear or multidimensional, crosslinking, solvent resistant oxazole, thiazole, or imidazole (i.e., heterocycle) oligomers and blends of the crosslinking oligomers and noncrosslinking comparable polymers are described. The oligomers are prepared by reacting tetraamines, diaminodiols, or diaminothiols (i.e. four-functional compounds) with poly-carboxylic acid halides, and crosslinking phenylimide end cap monomers in a suitable solvent under an inert atmosphere.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: October 23, 1990
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4948216
    Abstract: There is disclosed an optical device comprising a support having thereon a transparent amorphous layer of a low molecular weight organic compound, said layer having a glass transition temperature above about 50.degree. C. Also disclosed is a method for making the device including the step of vacuum depositing the organic compound on the support. Particularly preferred devices are integrated optical devices which include a pattern of a second index of refraction or effective index of refraction in the layer, which pattern can define an optical element.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: August 14, 1990
    Assignee: Eastman Kodak Company
    Inventors: John C. Brazas, Jr., Delwyn E. Machiele
  • Patent number: 4940802
    Abstract: A 4,4'-bis(phthalimido)diphenyl sulfone compound having the formula: ##STR1## wherein X is a halogen atom, k=0 to 4, l=0 to 4, m=0 to 4 and n=0 to 4, provided k+l+m+n>1.
    Type: Grant
    Filed: December 8, 1988
    Date of Patent: July 10, 1990
    Assignee: Tosoh Corporation
    Inventors: Takao Matsuba, Masashige Kubo, Takumi Kagawa, Kiyotaka Oyama, Koji Kawabata
  • Patent number: 4935523
    Abstract: Solvent resistance in polyimide, polyamide, and other resins can be improved by capping these resing with mono- or difunctional crosslinking end caps. Imidophenylamines of the general formula: ##STR1## wherein Y= ##STR2## R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;Me=methyl;T=allyl or methallyl;i=1 or 2;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --.comprise a new family of end cap monomers that are reactants in the synthesis of crosslinking, solvent resistant oligomers.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: June 19, 1990
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard