Benzene Ring Bonded Directly To The Ring Nitrogen Of The Five-membered Hetero Patents (Class 548/476)
  • Patent number: 4933467
    Abstract: Cyclic imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide and an amide in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: June 12, 1990
    Assignee: Eastman Kodak Company
    Inventors: Robert J. Perry, S. R. Turner
  • Patent number: 4933469
    Abstract: A method is provided for preparing oxybisphthalimides by heating a nitrophthalimide compound in the presence of an alkali metal carboxylate, a phase transfer catalyst and a nonpolar organic solvent.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: June 12, 1990
    Assignee: General Electric Company
    Inventors: Donald R. Berdahl, Pamela A. Matsch, Susan A. Nye
  • Patent number: 4933468
    Abstract: Amide-imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide having an isolated halogen function, and with an amine, in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: June 12, 1990
    Assignee: Eastman Kodak Company
    Inventors: Robert J. Perry, S. Richard Turner
  • Patent number: 4933466
    Abstract: Cyclic imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide and an amine in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium.Acyclic imides are prepared by reacting CO with an activated halide and an amide (primary or secondary) in the presence of a Pd catalyst and a base.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: June 12, 1990
    Assignee: Eastman Kodak Company
    Inventors: Robert J. Perry, Sam R. Turner
  • Patent number: 4873338
    Abstract: Compounds corresponding to Formula I ##STR1## wherein R.sup.1 denotes an acyl group andX denotes hydrogen, halogen, alkoxy, aroxy, SO.sub.3 H or a heterocyclic group attached through --O-- or --N<are prepared form a compound corresponding to Formula II ##STR2## wherein X has the meaning already indicated and Q denotes the group required for completing a dicarbonimide ringby reduction of the said compound to the amino compound and acylation into a compound corresponding to Formula III ##STR3## wherein X, Q and R.sup.1 have the meanings indicatedfollowed by conversion of the compound corresponding to Formula III into a compound corresponding to Formula I by hydrazinolytic or hydrolytic decomposition of the dicarbonimide ring.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: October 10, 1989
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Heinz Wiesen, Erich Wolff
  • Patent number: 4871475
    Abstract: Polysulfone and polyethersulfone oligomers are made by the condensation of phenols and halogenated moieties and exhibit improved solvent resistance when capped with crosslinkable end cap imidophenols. Composites made with a blend of the oligomers and corresponding polymers formed from the phenols and halogenated moieties, but without end caps, exhibit superior impact resistance while retaining the desired solvent resistance. Conductive or semiconductive oligomers (or their composites) can be formed by doping suitable oligomers, especially those prepared from Schiff base diols.
    Type: Grant
    Filed: October 7, 1985
    Date of Patent: October 3, 1989
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4868270
    Abstract: High thermal stabilities are achievable in linear or multidimensional sulfone, solvent resistant oligomers by incorporating oxazole, thiazole, or imidazole linkages into the oligomer backbone. Blended oligomers of crosslinking oligomers and noncrosslinking compatible polymers are also described. The oligomers include residues of four-functional compounds of the formula: ##STR1## wherein M=--CO--, --S--, --O--, --SO.sub.2 -- or --(CF.sub.3).sub.2 C--; andY=--OH, --SH, or --NH.sub.2.In an improved method, the reactants are condensed at or below ambient temperature in the presence of pyridine in a suitable solvent such as N,N'-dimethylacetamide (DMAC).
    Type: Grant
    Filed: November 17, 1987
    Date of Patent: September 19, 1989
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson
  • Patent number: 4861882
    Abstract: Ethynyl terminated imidothioethers (ETIs) are prepared by the reaction of a dimercaptan, such as 4,4'-dimercaptodiphenyl ether, and an ethynyl containing maleimide, such as N-(3-ethynylphenyl)maleimide. Blends of thse ETIs and ethynyl terminated polymeric materials, such as ethynyl terminated sulfones and ethynyl terminated arylene ethers, are also prepared. These resin blends exhibit excellent processability, and the cured blends show excellent fracture toughness and solvent resistance, as well as excellent adhesive and composite properties.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: August 29, 1989
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, John W. Connell, R. Gerald Bass
  • Patent number: 4851501
    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 compositions using the novel end caps are described for linear or multidimensional polyethersulfone oligomers.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: July 25, 1989
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4839378
    Abstract: Fluorophthalimide compounds represented by the following general formula (I): ##STR1## wherein R each stands for an ethyl group or an isopropyl group, are effective for controlling diseases of agricultural plants, especially diseases caused by microorganisms belonging to the genus Rhizoctonia, represented by sheath blight of rice plants, and diseases caused by Basidomycetes.
    Type: Grant
    Filed: April 28, 1987
    Date of Patent: June 13, 1989
    Assignee: Meiji Seika Kabushiki Kaisha
    Inventors: Masao Koyama, Michiaki Iwata, Kunihiko Kurihara, Masaji Sezaki
  • Patent number: 4780544
    Abstract: A method is provided for making oxybisphthalimides by heating an N-organonitrophthalimide in the presence of an aprotic organic solvent in an alkali metal carboxylate.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: October 25, 1988
    Assignee: General Electric Company
    Inventor: Donald R. Berdahl
  • Patent number: 4766243
    Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: August 23, 1988
    Assignee: Occidental Chemical Corporation
    Inventor: Michael J. Fifolt
  • Patent number: 4764217
    Abstract: Composition containing(a) an isoindoline pigment of the formula I ##STR1## and (b) a compound of the formula II ##STR2## Pigment mixtures of this kind, in particular when used in paints, are distinguished in particular by increased tinctorial strength and high lustre and especially by improved rheology.For the definition of the substituents and symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, Q, X, Y and Z, see claim 1.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: August 16, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Jost von der Crone, Bernhard Medinger, Philippe Bugnon
  • Patent number: 4755215
    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: January 14, 1986
    Date of Patent: July 5, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
  • Patent number: 4739030
    Abstract: The solvent resistance of polysulfone, polyether sulfone, and polyesters is enhanced by using difunctional end-cap monomers of the present invention to provide improved crosslinking. The imidophenol monomers include two unsaturated functionalities capable of crosslinking upon thermal or chemical activation. Oligomer, oligomer blends, pregregs, and composites using the novel end caps are also described.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: April 19, 1988
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4737512
    Abstract: Novel 4-(substituted-isoindol-2-yl)phenoxy-pentanoic and -heptanoic acids and derivatives which are useful as anti-arteriosclerotic agents are disclosed. The compounds elevate the high density lipoprotein fraction of cholesterol and also lower the low density lipoprotein fraction of cholesterol. Methods for preparing and using the compounds are included.
    Type: Grant
    Filed: October 27, 1986
    Date of Patent: April 12, 1988
    Assignee: Warner-Lambert Company
    Inventor: Milton L. Hoefle
  • Patent number: 4681949
    Abstract: Novel bis-aminopyridinium salts are useful as phase transfer catalysts in the preparation of aromatic ethers by the reaction of hydroxyaromatic compound alkali metal salts (e.g., bisphenol A disodium salt) with activated halo- or nitro-substituted aromatic compounds (e.g., 4-nitro-N-methylphthalimide). The bis-aminopyridinium salts may be prepared by the reaction of aminopyridines with bis-carbonium ion-generating compounds such as dibromoalkanes.
    Type: Grant
    Filed: April 30, 1986
    Date of Patent: July 21, 1987
    Assignee: General Electric Company
    Inventor: Daniel J. Brunelle
  • Patent number: 4667035
    Abstract: The novel compounds of the general formula I ##STR1## where R and R.sup.1 are substituents and the rings A can be substituted and/or can carry fused rings, are useful intermediates for the preparation of, for example, dyes and active ingredients.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: May 19, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Rolf-Dieter Kohler
  • Patent number: 4666936
    Abstract: Amide derivatives of 2-(p-aminobenzyl)-butyric acid and esters thereof having a hypolipidemizing and hypocholesterolemizing pharmaceutical activity and their preparation are described.Included are compounds of the formula ##STR1## wherein R and R' together represent the group ##STR2## or the group ##STR3## and R" is hydrogen or a 1 to 6 carbon alkyl group.
    Type: Grant
    Filed: August 7, 1985
    Date of Patent: May 19, 1987
    Assignee: Medosan Industrie Biochimiche Riunite S.p.A.
    Inventor: Alessandro Baglioni
  • Patent number: 4661630
    Abstract: Described herein are novel carboxylic acid amide compounds or carboximide compounds represented by the general formula: ##STR1## wherein Z represents either the monoamido radical of an aromatic or cycloaliphatic ortho dicarboxylic acid or the amide of the corresponding anhydride, and their pharmaceutically acceptable salts; processes for the production thereof; and medicines containing the same. The novel compounds are useful as treating, preventing and improving agents for diseases attended with cerebral dysfunction as well as various symptoms caused by the said diseases.
    Type: Grant
    Filed: December 2, 1985
    Date of Patent: April 28, 1987
    Assignee: Eisai Co., Ltd.
    Inventors: Yasuji Harigaya, Hiroo Ogura, Mitsuo Mihara, Motosuke Yamanaka, Kiyomi Yamatsu
  • Patent number: 4632949
    Abstract: The present invention relates to novel N-(alkoxyphenyl) phthalimides conforming to the structure ##STR1## wherein X is a halogen atom, R is a C.sub.1 -C.sub.4 alkyl, g is 1 to 5, n is an integer of from 0 to 4, m is either 0 or 1 and p is either 0 or 1. The phthalimide thus disclosed was found to be suitable as a flame retarding additive for thermoplastic molding compositions, especially compositions comprising polycarbonate resins.
    Type: Grant
    Filed: December 31, 1984
    Date of Patent: December 30, 1986
    Assignee: Mobay Chemical Corporation
    Inventor: Sivaram Krishnan
  • Patent number: 4617316
    Abstract: Insecticidal compounds of the formula: ##STR1## in which A is chloro and B is hydrogen or A and B are both fluoro, X is oxygen or sulfur and one of R.sup.1 and R.sup.2 is or includes an optionally substituted 5-membered heteroaryl ring, their method for preparation and formulation, insecticidal compositions thereof, and their use to control insects, are disclosed and exemplified.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: October 14, 1986
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4615832
    Abstract: The present invention relates to new phthalimides of the formula (I) ##STR1## wherein n is an integer of from 1 to 12, preferably 1 to 4 and especially 1 to 2 andR is H or F,and their preparation, these phthalimides being suitable, in combination with alkali metal salts, as flameproofing agent combinations for thermoplastic, branched, aromatic polycarbonates.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: October 7, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jurgen Kress, Klaus Kircher
  • Patent number: 4605745
    Abstract: A method is provided for making aromatic ethers by effecting the displacement of reactive radicals on an activated aromatic nucleus such as a phthalimide with a mono or bisalkali metal phenoxide in the presence of an organic solvent and a dialkylamino branched alkyl substituted pyridinium salt as a phase transfer catalyst. Improved yields of bis(aromatic ethers) are achieved without the production of undesirable by-products, such as akylated phenols.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: August 12, 1986
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Daniel A. Singleton
  • Patent number: 4577033
    Abstract: Heterocyclic quaternary ammonium salts such as N,N-di-n-butylpiperidinium bromide are excellent phase transfer agents for the preparation of aromatic ethers, as by the reaction of the disodium salt of bisphenol A with 4-nitro-N-methylphthalimide.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: March 18, 1986
    Assignee: General Electric Company
    Inventors: John W. Verbicky, Jr., Alice M. Colley
  • Patent number: 4554357
    Abstract: Bis-quaternary ammonium and phosphonium salts such as bis(tri-n-butyl)-1,6-hexylenediammonium dibromide are excellent phase transfer agents for the preparation of aromatic ether imides, as by the reaction of the disodium salt of bisphenol A with 4-nitro-N-methylphthalimide.
    Type: Grant
    Filed: October 14, 1983
    Date of Patent: November 19, 1985
    Assignee: General Electric Company
    Inventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Jr.
  • Patent number: 4533739
    Abstract: This invention relates to the novel use of certain aromatic substituted amidines as antidiarrheals.
    Type: Grant
    Filed: October 12, 1982
    Date of Patent: August 6, 1985
    Assignee: G. D. Searle & Co.
    Inventors: Barnett S. Pitzele, Stella S. T. Yu, Robert W. Hamilton, Alan E. Moormann
  • Patent number: 4520204
    Abstract: The yield of aromatic ether imides prepared by reacting a substituted phthalimide (such as 4-nitro-N-methylphthalimide) with an alkali metal salt of a hydroxyaromatic compound (such as the disodium salt of bisphenol A) in the presence of a phase transfer catalyst is improved by conducting the reaction in o-dichlorobenzene as diluent. When the reaction mixture is subsequently extracted with water and/or aqueous alkali, o-dichlorobenzene can also be used in recovery of the phase transfer catalyst from the aqueous phase by extraction thereof. Such recovery is improved by dissolving a substantial amount of inorganic salt in the aqueous phase and by conducting the o-dichlorobenzene extraction at elevated temperatures.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: May 28, 1985
    Assignee: General Electric Company
    Inventor: Thomas L. Evans
  • Patent number: 4513141
    Abstract: A method is provided for making aromatic ethers by effecting the displacement of reactive radicals on an activated aromatic nucleus such as a phthalimide with a mono or bisalkali metal phenoxide in the presence of an organic solvent and a dialkylamino branched alkyl substituted pyridinium salt as a phase transfer catalyst. Improved yields of bis(aromatic ethers) are achieved without the production of undesirable by-products, such as alkylated phenols.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: April 23, 1985
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Daniel A. Singleton
  • Patent number: 4489185
    Abstract: Novel carbinol-containing polyimides capable of self-crosslinking at low temperatures are prepared by reacting a molar excess of selected 3,3',4,4'-benzhydrol tetracarboxylic acid compounds (the tetraacid, diester-diacid, or (dianhydride) with polyfunctional polyamines (e.g. 4,4'-methylenedianiline, 1,6-hexanediamine, etc.) in an inert organic solvent at about 100.degree.-150.degree. C. The molar ratio of tetracarboxylic acid compound to diamine must be between 2:1 and 9:8. The polyimides may be crosslinked at less than 200.degree. C. via a reaction between the carbinol group(s) and the end group(s) of the polyimide.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: December 18, 1984
    Inventor: Jules E. Schoenberg
  • Patent number: 4480105
    Abstract: Novel compounds of the formula II ##STR1## are described, in which M.sub.1 and M.sub.2 individually are --OH or together are --O--, X is --NO.sub.2, --OR', --SR' or SO.sub.2 R' and the (R')s independently of one another are C.sub.1-20 -alkyl, C.sub.3-5 -alkenyl, C.sub.3-5 -alkynyl, C.sub.2-4 -monohydroxyalkyl, C.sub.1-12 -halogenoalkyl, benzyl, C.sub.5-12 -cycloalkyl, phenyl, carboxyphenyl, halogenophenyl, nitrophenyl, alkyl- or alkoxy-phenyl each having 1-4 C atoms in the alkyl or alkoxy moieties, or acetylaminophenyl, such as for example 3-n-butylthio-5-nitrophthalic anhydride. The compounds (II) in which M.sub.1 and M.sub.2 together are --O-- are suitable as sensitizers for photo-crosslinkable polymers or as initiators for the photopolymerization of ethylenically unsaturated compounds or for the photochemical crosslinking of polyolefins, and those where M.sub.1 and M.sub.2 are --OH are useful intermediates for those wherein M.sub.1 and M.sub.2 together are --O--.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: October 30, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Fischer, Vratislav Kvita, Hans Zweifel
  • Patent number: 4476309
    Abstract: A method for making aromatic ether imides is provided by effecting the displacement of reactive radicals on a phthalimide nucleus with a mono- or bis-alkali metal phenoxide in the presence of a nonpolar solvent and a phase transfer catalyst, such as a triorganoborate. The aromatic ether imide made by the present invention are useful intermediates for making aromatic ether anhydrides and aromatic bis(ether anhydrides).
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: October 9, 1984
    Assignee: General Electric Company
    Inventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Jr.
  • Patent number: 4476184
    Abstract: Resins are prepared from polymers that bear monofunctional or difunctional groups derived from compounds that are condensation products of amino-phenols and acid anhydrides. The polymers are prepared by coreacting aromatic compounds holding two hydroxyl groups, aromatic compounds holding two active halogen groups, and the condensation product of amino-phenol and acid anhydride, the condensation product holding one hydroxyl group. The resulting product has a molecular weight between about 1,000 and 40,000, preferably between about 5,000 and 30,000, and can be cross-linked to form a resin that is thermoplastic and solvent resistant.
    Type: Grant
    Filed: August 9, 1983
    Date of Patent: October 9, 1984
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4471125
    Abstract: A method is provided for making aromatic ether imides in the substantial absence of a solvent. A mixture of at least one halo-substituted phthalimide and at least one anhydrous alkali metal phenoxide salt is heated at a temperature at least sufficient to convert the halo-substituted phthalimide to the molten state and below the temperature at which the alkali metal phenoxide is thermally unstable.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: September 11, 1984
    Assignee: General Electric Company
    Inventors: John W. Verbicky, Jr., Brent A. Dellacoletta
  • Patent number: 4467100
    Abstract: Imide-amides having the structure ##STR1## wherein ##STR2## are certain cycloaliphatic or aromatic groups and R and R individually are hydrogen, halogen, an alkyl group having from 1 to 4 carbon atoms, hydroxy, carboxyl, and amine and when taken together represent ##STR3## wherein R.sup.2 is the same as R and R.sup.1, have been found to provide cured epoxy resin systems characterized by high temperature stability and excellent mechanical and physical properties.
    Type: Grant
    Filed: July 21, 1982
    Date of Patent: August 21, 1984
    Assignee: Lord Corporation
    Inventors: Raj N. Gounder, John T. Geary
  • Patent number: 4428977
    Abstract: A water soluble composition including an amine or ammonium salt of a polyimide precursor which is obtained by the reaction steps of: reacting a tetracarboxylic compound and a diamine in about equimolar amounts in a water miscible organic solvent to obtain the polyimide precursor; and reacting the polyimide precursor with ammonia, or an aqueous solution of ammonia, or a primary or secondary aliphatic amine in an amount sufficient to neutralize the free carboxyl groups of the polyimide precursor.A process of coating and a substrate are also disclosed.
    Type: Grant
    Filed: September 24, 1976
    Date of Patent: January 31, 1984
    Assignee: General Electric Company
    Inventor: Marvin A. Peterson
  • Patent number: 4414269
    Abstract: Resins are prepared from polysulfone and polyethersulfone polymers that bear functional groups derived from compounds that are condensation products of amino-phenols and acid anhydrides. The polymers are prepared by coreacting aromatic compounds holding two hydroxyl groups, aromatic compounds holding two active halogen groups, and the condensation product of amino-phenol and acid anhydride, the condensation product holding one hydroxyl group. The resulting product has a molecular weight between about 1,000 and 40,000, preferably between about 5,000 and 30,000, and can be cross-linked to form a resin that is thermoplastic and solvent resistant.
    Type: Grant
    Filed: June 16, 1981
    Date of Patent: November 8, 1983
    Assignees: TRW, Inc., The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 4396516
    Abstract: This invention is a lubricant comprising an imide compound obtained by reacting a dibasic acid selected from the group consisting of succinic acid, maleic acid, glutaric acid and phthalic acid with a primary amine having a C.sub.8 -C.sub.18 hydrocarbon radical.The lubricant of the invention may be used in combination with a specified diamine derivative and known lubricant additives, and exhibits excellent lubricating properties.
    Type: Grant
    Filed: June 9, 1981
    Date of Patent: August 2, 1983
    Assignee: Nippon Oil Company, Ltd.
    Inventors: Hirotsugu Kinoshita, Hiroshi Uemura, Makoto Sekiya, Kazuyoshi Mitamura
  • Patent number: 4380466
    Abstract: A novel hexahydroisoindole derivative of the formula, ##STR1## which can be produced by dehydration of the corresponding 3a-hydroxy-octahydroisioindole derivative or by reaction of the corresponding 3-chloro-hexahydroisoindole with a thiol sulfonate.The derivative is useful as an intermediate for producing a compound having a substituted or unsubstituted thiol group at 3-position and can be utilized as a herbicide possessing low toxicity to crops and animal.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: April 19, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventor: Yasuo Ishida
  • Patent number: 4363917
    Abstract: Novel compounds of the formula I or II ##STR1## are described, in which M.sub.1 and M.sub.2 individually are --OH or together are --O--, R is hydrogen, C.sub.1-20 -alkyl, C.sub.2-5 -alkenyl, C.sub.3-5 -alkynyl, C.sub.5-12 -cycloalkyl, benzyl, phenyl or toluyl, X is --NO.sub.2, --OR', --SR' or --SO.sub.2 R' and the (R')s independently of one another are C.sub.1-20 -alkyl, C.sub.3-5 -alkenyl, C.sub.3-5 -alkynyl, C.sub.2-4 -monohydroxyalkyl, C.sub.1-12 -halogenoalkyl, benzyl, C.sub.5-12 -cycloalkyl, phenyl, carboxyphenyl, halogenophenyl, nitrophenyl, alkyl- or alkoxy-phenyl each having 1-4 C atoms in the alkyl or alkoxy moieties, or acetylaminophenyl. The compounds (I) and compounds (II) in which M.sub.1 and M.sub.2 together are --O-- are suitable as sensitizers for photocrosslinkable polymers or as initiators for the photopolymerization of ethylenically unsaturated compounds or for the photochemical crosslinking of polyolefins.
    Type: Grant
    Filed: April 28, 1981
    Date of Patent: December 14, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Fischer, Vratislav Kvita, Hans Zweifel