The Ring Nitrogen Of The Five-membered Hetero Ring Is Unsubstituted Or Hydrocarbyl Substituted Only Patents (Class 548/480)
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Patent number: 4883655Abstract: The invention relates primarily to quaternized polycyclic compounds having the formula ##STR1## wherein m is an integer having a value of from 1 to 4; R is alkylene having from 3 to 8 carbon atoms and is optionally substituted with C.sub.1 to C.sub.4 alkyl; R.sub.2 together with the quaternary nitrogen, forms a 5 to 14 membered heterocyclic ring, said ring containing from 1 to 2 hetero atoms selected from the group of nitrogen, sulfur and oxygen; R.sub.1 forms a double bond in the heterocyclic ring of the quaternized nitrogen or is alkyl, alkyleneoxyalkyl, alkylhydroxy, aryl, aralkyl, aralkenyl, alkaryl, alkylamidoalkyl and X.sup.- is a chloride, bromide or iodide anion. The invention also relates to the preparation and use of said quaternized polycyclic compounds.Type: GrantFiled: August 28, 1987Date of Patent: November 28, 1989Assignee: GAF CorporationInventors: Robert B. Login, Ratan K. Chaudhuri, David J. Tracy, Michael W. Helioff
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Patent number: 4837307Abstract: A 2,2'-bridged[1,1'-biphenyl]-3-ylmethyl compound of the following formula is an intermediate to insecticidal esters. ##STR1## wherein n is 1-4 and Y is a leaving group readily displaced by carboxylate anions.Type: GrantFiled: January 16, 1984Date of Patent: June 6, 1989Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4835272Abstract: A process for formation of a base, which comprises reacting an acetylide compound with a salt. The acetylide compound has the following formula:(R--C.tbd.C--).sub.n Mwherein R is a monovalent group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heterocyclic group, each of which may have one or more substituent groups; M is an n-valent transition metal atom; and n is 1, 2 or 3. The salt is composed of an anion having an affinity for the transition metal (M) (the affinity of the anion for the transition metal is more than that of the acetylide anion (R--C.tbd.C.crclbar.)), and a cation derived from one selected from the group consisting of an alkali metal, an alkaline earth metal, ammonia and an organic base. A light-sensitive material containing the acetylide compound and the salt is also disclosed.Type: GrantFiled: July 16, 1987Date of Patent: May 30, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Shunichi Ishikawa, Ken Kawata
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Patent number: 4780544Abstract: 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: GrantFiled: July 2, 1986Date of Patent: October 25, 1988Assignee: General Electric CompanyInventor: Donald R. Berdahl
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Patent number: 4711964Abstract: Resins are prepared by polymerization of compounds of the formula ##STR1## where R is a divalent linking group. Blends of a compound of the formula (I) as defined above and a bis-maleimide of the formula ##STR2## where Ar' is an aromatic linking group.Type: GrantFiled: May 8, 1986Date of Patent: December 8, 1987Assignee: University of DaytonInventors: Loon-Seng Tan, Fred E. Arnold
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Patent number: 4681949Abstract: 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: GrantFiled: April 30, 1986Date of Patent: July 21, 1987Assignee: General Electric CompanyInventor: Daniel J. Brunelle
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Patent number: 4680412Abstract: Fluorophthalimides are prepared by a process in which a fluorophthalic anhydride is reacted, in the presence of an aliphatic sulfone, with from 0.4 to 0.8 mole of urea per mole of fluorophthalic anhydride, and the reaction is carried out first at 110.degree.-140.degree. C. and then at 150.degree.-170.degree. C.Type: GrantFiled: May 31, 1984Date of Patent: July 14, 1987Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Juergen Varwig, Wolfgang Rohr
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Patent number: 4623732Abstract: Compounds which are bis-(N-alkylphthalimides) are prepared by a new process in which a halogen-containing precursor is heated in the presence of a nickel compound, a reducing agent, for example, metallic zinc, and an organic solvent. The resulting compound is useful in a process for the preparation of a copolymer, in which the compound is reacted with alkali to form a tetraacid, the acid is dehydrated to form a dianhydride, and the dianhydride is reacted with a second dianhydride and a diamine under copolymer-forming conditions.Type: GrantFiled: November 18, 1983Date of Patent: November 18, 1986Assignee: General Electric CompanyInventor: Edward N. Peters
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Patent number: 4609741Abstract: Novel phthalic acid derivatives are described which are substituted by 2-propynyloxy groups, of the formula I ##STR1## in which Q.sub.1, and Q.sub.2 independently of one another are --OH or --O.sup.- M.sup.+, or Q.sub.1 and Q.sub.2 together form the grouping --O--, [O.sup.- ].sub.2 M.sub.1.sup.++ or --N(R.sub.2)--, M.sup.+ is an alkali metal ion, a trialkyl ammonium ion having 3-24 carbon atoms or a quaternary ammonium ion and M.sub.1.sup.++ is an alkaline earth metal ion, R.sub.2 is an alkyl group or an unsubstituted or substituted aryl group, n is 1 or 2 and R.sub.1 is hydrogen, if n is 1, or a direct bond, if n is 2, are described. The phthalic anhydrides which are substituted by 2-propynyloxy, of the formula I, can be used for curing epoxy resins, cured products with outstanding physical properties being obtained.Type: GrantFiled: August 9, 1984Date of Patent: September 2, 1986Assignee: Ciba-Geigy CorporationInventors: Roland Darms, Vratislav Kvita, Charles E. Monnier
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Patent number: 4605745Abstract: 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: GrantFiled: December 24, 1984Date of Patent: August 12, 1986Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Daniel A. Singleton
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Patent number: 4585876Abstract: Novel xanthones and thioxanthones of the formula I ##STR1## in which A, X, Y, Z, E and E' are as defined in patent claim 1, are described. A is preferably --S-- and E and E' are preferably bonded in the ortho-position relative to one another. The compounds (I) are suitable, for example, as sensitizers for photocrosslinkable polymers or photocurable compositions, or for use in mixtures with polymers with H donor groups for image formation, in particular electrically conductive coatings and patterns, by means of electroless deposition of metals.Type: GrantFiled: November 14, 1983Date of Patent: April 29, 1986Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Jurgen Finter, Hans Zweifel
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Patent number: 4554357Abstract: 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: GrantFiled: October 14, 1983Date of Patent: November 19, 1985Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Jr.
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Patent number: 4513141Abstract: 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: GrantFiled: April 28, 1983Date of Patent: April 23, 1985Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Daniel A. Singleton
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Patent number: 4511722Abstract: Cyclic N-vinylacylamines are prepared by heating carbonic acid esters of cyclic N-2-hydroxyethylacylamines in the presence of a catalytic amount of alkali or alkaline earth metal compound having an alkaline reaction and subsequently distilling the reaction mixture.Cyclic N-vinylacylamines are valuable precursors for preparing plant protection agents and medicaments and serve as polymerization and copolymerization components for preparing plastics, surface coatings, paints and ion exchange materials.Type: GrantFiled: February 16, 1983Date of Patent: April 16, 1985Assignee: Bayer AktiengesellschaftInventors: Heinrich Krimm, Hans-Josef Buysch, Peter M. Lange, Reinhold Klipper
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Patent number: 4480105Abstract: 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: GrantFiled: April 30, 1982Date of Patent: October 30, 1984Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Vratislav Kvita, Hans Zweifel
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Patent number: 4477675Abstract: The process of preparing a compound of the formula: ##STR1## wherein, Y and Z are each H, alkyl, halo, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;X is F, Cl, Br, or NR.sub.1 R.sub.2 wherein R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkynyl, alkenyl, cycloalkyl, aryl or aralkyl; andR is H, alkyl, cycloalkyl, or aralkyl; which comprises the step of oxidation of the corresponding 3-desoxy compound.Type: GrantFiled: September 7, 1982Date of Patent: October 16, 1984Assignee: USV Pharmaceutical CorporationInventors: Joseph Auerbach, Frederick A. Golec, Jr.
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Patent number: 4476309Abstract: 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: GrantFiled: March 21, 1983Date of Patent: October 9, 1984Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Jr.
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Patent number: 4465842Abstract: The N-benzylimides having the structural formula: ##STR1## wherein Ar comprises a benzene radical and R.sub.1 is an aliphatic or aromatic hydrocarbon, are prepared in good yield by reacting a compound having the structural formula:ArH (II)with a compound having the structural formula: ##STR2## in the presence of hydrofluoric acid.Type: GrantFiled: May 14, 1982Date of Patent: August 14, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Michel Desbois, Michel Reppelin
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Patent number: 4419519Abstract: A process for the continuous preparation of phthalimide by reacting phthalic anhydride with ammonia in about the stoichiometric ratio, in a mixing apparatus and subsequently in a reaction tube at a particular flow velocity and a particular temperature.The phthalimide obtainable by the process of the invention is a valuable starting material for the preparation of dyes, pesticides and pigments, especially copper phthalocyanines.Type: GrantFiled: June 29, 1981Date of Patent: December 6, 1983Assignee: BASF AktiengesellschaftInventors: Gerhard Kilpper, Johannes Grimmer
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Patent number: 4363917Abstract: 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: GrantFiled: April 28, 1981Date of Patent: December 14, 1982Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Vratislav Kvita, Hans Zweifel