Preparing Directly By Condensing A Primary Amine Patents (Class 564/435)
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Patent number: 7563548Abstract: An amine compound represented by the general formula (1), which is incorporated as a charge-transporting substance to a charge-transporting layer of an electrophotographic photoreceptor: (in which Ar1, Ar2 and Ar3 each represents an optionally-substituted aryl group, or an optionally-substituted monovalent heterocyclic ring residue. Ar4 represents an optionally-substituted arylene group, or an optionally-substituted bivalent heterocyclic ring residue. R1 represents an optionally-substituted alkyl group, an optionally-substituted aryl group, an optionally-substituted monovalent heterocyclic ring residue, or an optionally-substituted aralkyl group. R2 and R3 each represents a hydrogen atom, an optionally-substituted alkyl group, an optionally-substituted aryl group, an optionally-substituted monovalent heterocyclic ring residue, or an optionally-substituted aralkyl group. n represents an integer of 1 or 2.Type: GrantFiled: November 30, 2004Date of Patent: July 21, 2009Assignee: Sharp Kabushiki KaishaInventors: Akihiro Kondoh, Takatsugu Obata
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Publication number: 20090156864Abstract: The invention teaches novel process steps for the rapid high yield manufacture of diphenylamines of the formula wherein R1 is selected from hydrogen, alkyl, and aryl; wherein each R2 and R3 is the same or different and each is independently selected from hydrogen, alkyl, alkoxy, aralkyl, dialkylamino, alkylarylamino and substituted or unsubstituted aryl, the substituents on aryl being each independently selected from alkyl (C1-C8), alkoxy (C1-C8), aroxy, aralkoxy and halogen; wherein n and m are each independently an integer from 1 to 5. Diphenylamines are key intermediates for the production of leuco dyes used in pressure-sensitive and heat-sensitive imaging systems.Type: ApplicationFiled: February 19, 2009Publication date: June 18, 2009Applicant: Appleton Papers Inc.Inventor: Ponnampalam Mathiaparanam
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Patent number: 7413682Abstract: Antioxidants for industrial, automotive, and aviation lubricants and methods of making the same are provided. A process using alkylated diphenylamines; alkylated phenyl-?-naphthyl amines; and a metal catalyst to form oxidates is provided. The metal catalyst is a combination of a cation and an organic anion, for example, a metal acetylacetone. The reaction takes place in the presence of oxygen to form an antioxidant comprising oligomers of the alkylated diphenylamine and the alkylated phenyl-?-naphthyl amine, and a metal component of the catalyst.Type: GrantFiled: August 15, 2006Date of Patent: August 19, 2008Assignee: Anderol, Inc.Inventor: Eugene P. DiBella
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Patent number: 6972287Abstract: The present invention provides a method of treating Alzheimer's disease using a compound of Formula (I). Also provided is a method of inhibiting the aggregation of amyloid proteins using a compound of the Formula (I) and a method of imaging amyloid deposits, as well as new compounds of Formula (I).Type: GrantFiled: May 31, 2000Date of Patent: December 6, 2005Assignee: Pfizer Inc.Inventors: Corinne Elizabeth Augelli-Szafran, Mark Robert Barvian, Christopher Franklin Bigge, Shelly Ann Glase, Shunichiro Hachiya, John Steven Kiely, Takenori Kimura, Yingjie Lai, Annette Theresa Sakkab, Mark James Suto, Larry Craswell Walker, Tomoyuki Yasunaga, Nian Zhuang
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Publication number: 20040143138Abstract: The present invention relates to a process for the preparation of nitrodiphenyl-amines by reaction of nitrohalogens with anilines a base and a catalyst, and to a process for the preparation of aminodiphenylamine by hydrogenation of the nitrodiphenylamine intermediately prepared.Type: ApplicationFiled: January 2, 2004Publication date: July 22, 2004Inventors: Klaus Kunz, Joachim Haider, Dirk Ganzer, Ulrich Scholz, Adolf Sicheneder
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Publication number: 20040143139Abstract: The present invention relates to a process for the production of aminodiphenyl-amines, such as 4-aminodiphenylamine (4-ADPA), by reacting nitrohalogenated benzenes with anilines in the presence of a base as well as a copper-phosphorus complex, followed by hydrogenation of the intermediately formed nitrodiphenyl-amines.Type: ApplicationFiled: January 2, 2004Publication date: July 22, 2004Inventors: Adolf Sicheneder, Ulrich Scholz, Joachim Haider
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Publication number: 20020128515Abstract: An organic electroluminescent device comprising: an organic thin-film transistor element including at least an active layer made of an organic material; and an organic electroluminescent element driven by the organic thin-film transistor element.Type: ApplicationFiled: November 2, 2001Publication date: September 12, 2002Inventors: Masaya Ishida, Masahiro Furusawa, Katsuyuki Morii, Osamu Yokoyama, Satoru Miyashita, Tatsuya Shimoda
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Patent number: 6387949Abstract: Compounds of general formula I are disclosed and claimed in the present application, as well as their pharmaceutically acceptable salts, pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain.Type: GrantFiled: June 1, 2000Date of Patent: May 14, 2002Assignee: AstraZeneca Canada Inc.Inventors: Daniel Delorme, Vlad Gregor, Niklas Plobeck, Edward Roberts, Eric Sun
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Patent number: 6365776Abstract: The present invention provides an activator in arylamination using a palladium compound as a catalyst, which is superior to conventional phosphines in stability and performance. With the phosphine sulfide as an activator, an arylamination reaction achieves improved selectivity to produce a desired aromatic amine in an obviously increased yield as compared with a reaction using the corresponding phosphine compound. Moreover, the phosphine sulfide of the invention is impervious to oxidation and exists stably in air and therefore sufficiently withstands use on an industrial scale.Type: GrantFiled: September 6, 2001Date of Patent: April 2, 2002Assignee: Takasago International CorporationInventors: Mitsuhiko Fujiwara, Ken Suzuki, Tohru Kobayashi, Yoji Hori, Toshimitsu Hagiwara
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Patent number: 6291702Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be colorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: February 8, 2000Date of Patent: September 18, 2001Assignee: Florida International UniversityInventor: David Alan Becker
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Patent number: 6221414Abstract: The invention relates to a process for treating fruit and vegetables after harvesting, using, as plant-protection treatment composition, the mixture with water of the reaction medium resulting from the implementation of steps of purification of a plant-protection product contaminated with impurities of aromatic primary amine type. The process contains the steps of: a) the placing in contact with stirring, at a temperature between 15 and 25° C., of an aqueous solution of an alkali metal nitrite with an organic solution prepared by dissolving the said plant-protection product to be purified in a solvent chosen from a nonionic surfactant, a C2-C12 glycol and mixtures thereof; b) the addition of a strong inorganic acid to the resulting reaction medium, while stirring at the said temperature; c) followed by heating of the reaction medium to a temperature of between 30 and 70° C.Type: GrantFiled: August 27, 1999Date of Patent: April 24, 2001Assignee: Xeda InternationalInventor: Alberto Sardo
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Patent number: 6218576Abstract: Described is a process for producing a diarylamine, which comprises subjecting an arylamine to condensation reaction in the co-presence of anhydrous aluminum chloride and anhydrous calcium chloride. The process permits the production of a diarylamine in a high yield at a normal pressure while terminating the reaction in a short time; and also permits the production, at a low cost, of a diarylamine having a high purity to be usable sufficiently as an intermediate for the production of a raw material for an electronic material.Type: GrantFiled: June 5, 2000Date of Patent: April 17, 2001Assignee: Sankio Chemical Co., Ltd.Inventors: Taichi Shintou, Satoru Fujii, Shinji Kubo
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Patent number: 6197825Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be calorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: May 28, 1998Date of Patent: March 6, 2001Assignee: Florida International UniversityInventor: David Alan Becker
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Patent number: 5902901Abstract: A process for the preparation of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine which comprises the reaction of N,N-bis(3,4-dimethylphenyl)amine and an iodobiphenyl in the presence of a ligand copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of, for example, from about 120.degree. C. to about 150.degree. C.Type: GrantFiled: May 7, 1998Date of Patent: May 11, 1999Assignee: Xerox CorporationInventors: H. Bruce Goodbrand, George Liebermann, Roger E. Gaynor
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Patent number: 5723669Abstract: A process preparation of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine which comprises the reaction of N,N-bis(3,4-dimethylphenyl)amine and an iodobiphenyl in the presence of a ligand copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of from about 120.degree. C. to about 150.degree. C.Type: GrantFiled: January 30, 1997Date of Patent: March 3, 1998Assignee: Xerox CorporationInventors: H. Bruce Goodbrand, Nan-Xing Hu, Beng S. Ong
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Patent number: 5723671Abstract: A process for the preparation of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine which comprises the reaction of an aminobiphenyl and an iodoxylene in the presence of a ligand copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of from about 120.degree. C. to about 150.degree. C.Type: GrantFiled: January 30, 1997Date of Patent: March 3, 1998Assignee: Xerox CorporationInventors: H. Bruce Goodbrand, Nan-Xing Hu, Beng S. Ong
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Patent number: 5705697Abstract: A process for the preparation of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine which comprises the reaction of N-(3,4-dimethylphenyl)-4-biphenylamine and an iodoxylene in the presence of a ligated copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of from about 120.degree. C. to about 150.degree. C.Type: GrantFiled: January 30, 1997Date of Patent: January 6, 1998Assignee: Xerox CorporationInventors: H. Bruce Goodbrand, Nan-Xing Hu, Beng S. Ong
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Patent number: 5654483Abstract: A process for producing an alkoxy-substituted tri-phenylamine comprising reacting an alkoxy-substituted cyclohexanone with a diphenylamine or an aniline, while forming said cyclohexanone in the same system from an alkoxy-substituted phenol by using said phenol as a hydrogen acceptor, in the presence of a hydrogen transfer catalyst and a catalytic amount of the alkoxy-substituted cyclohexanone corresponding to the alkoxy-substituted phenol used for the reaction, or after converting partially the alkoxy-substituted phenol to a catalytic amount of the alkoxy-substituted cyclohexanone under a hydrogen pressure in the presence of a hydrogen transfer catalyst, wherein a surface-supported catalyst is used as the hydrogen transfer catalyst.Type: GrantFiled: December 19, 1995Date of Patent: August 5, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Chiyuki Kikuchi, Hiroshi Naruse, Masaru Wada, Teruyuki Nagata
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Patent number: 5648538Abstract: A process for preparing diarylamines in high yield, in which diarylamines are prepared from arylamines in the presence of a solid acid catalyst. The solid acid catalyst with good stability and regeneration ability consists of H-type beta zeolite and active alumina, the ratio of SiO.sub.2 /Al.sub.2 O.sub.3 in the zeolite is 20.about.100, and the content of active alumina is 10%.about.70% (wt).Type: GrantFiled: June 29, 1995Date of Patent: July 15, 1997Assignees: Fushun Research Institute of Petroleum and Petrochemicals, China Petrochemical Corp.Inventors: Xiusen Liu, Huarong Zhu, Fubin Ai, Lizhi Song, Zhihui Lu, Xuewei Hou
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Patent number: 5602284Abstract: Aminobiphenyl (ABP) can be separated off from diphenylamine (DPA) by treating the DPA to be purified at elevated temperature with a substance in which oxygen is bonded by a double bond to a C atom, an N atom or another O atom and then separating off the DPA from the treated mixture.Type: GrantFiled: September 11, 1995Date of Patent: February 11, 1997Assignee: Bayer AktiengesellschaftInventors: Frank Arndt, Hans-Josef Buysch, Rudolf Wiemers
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Patent number: 5545752Abstract: A processes for the preparation of diphenylamine or a nucleus-substituted derivative thereof, which comprise, upon feeding into a reaction system a phenol compound and reacting in the reaction system a cyclohexanone compound with an aniline compound in the presence of a hydrogen transfer catalyst and a catalytic amount of the cyclohexanone compound corresponding to the phenol compound while using the phenol compound as a hydrogen acceptor and forming the cyclohexanone compound in the reaction system, (1) conducting reaction while adding dropwise the aniline compound and (2) employing a hydroxide, carbonate or bicarbonate of an alkali metal and/or alkaline earth metal when the hydrogen transfer catalyst is one of noble metals of Group VIII of the periodic table, respectively.Type: GrantFiled: June 2, 1995Date of Patent: August 13, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada
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Patent number: 5495049Abstract: A triarylamine compound useful as a charge transport material of an electrophotographic photoreceptor, which represented by formula (I) ##STR1## wherein Ar.sub.1 and Ar.sub.2 each represents a phenyl group or a condensed ring group.Type: GrantFiled: March 22, 1994Date of Patent: February 27, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Akira Imai, Ryosaku Igarashi
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Patent number: 5451702Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.Type: GrantFiled: April 26, 1993Date of Patent: September 19, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5072045Abstract: The invention relates to an improved process for producing alkenylated aromatic amines which involves the catalytic reaction of an aromatic amine with a diene. The improvement resides in using a solvent in which the aromatic amine and diene are soluble in the proportions present in the reaction but inert to the reaction.Type: GrantFiled: December 21, 1987Date of Patent: December 10, 1991Assignee: Air Products and Chemicals, Inc.Inventors: William F. Burgoyne, Jr., Dale D. Dixon
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Patent number: 4952731Abstract: Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in th presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol.The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone.The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product.Type: GrantFiled: August 15, 1988Date of Patent: August 28, 1990Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Akihiro Tamaki, Nobuyuki Kajimoto, Masaru Wada
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Patent number: 4814504Abstract: Diphenylamine is produced by contacting aniline with an alumina catalyst having at least about 30 percent by volume of its total porosity in the form of pores having a diameter of between about 120 and about 200 Angstroms and a sulfur content, as measured in the form of SO.sub.4, of less than about 0.02 percent by weight at between about 380.degree. and 475.degree. C.Type: GrantFiled: September 3, 1986Date of Patent: March 21, 1989Assignee: Uniroyal Chemical Company, Inc.Inventor: Russell E. Malz, Jr.
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Patent number: 4804783Abstract: Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in the presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol.The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone.The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product.Type: GrantFiled: July 31, 1987Date of Patent: February 14, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Akihiro Tamaki, Nobuyuki Kajimoto, Masaru Wada
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Patent number: 4782185Abstract: With a far shorter reaction time, azeotropic distillation of the water in the condensation of 4-nitrohalogenobenzenes and primary aromatic amines or formyl derivatives thereof in the presence of potassium carbonate and, if appropriate, copper compounds can be dispensed with if the reaction is carried out in the presence of Al metal, Mg metal or Zn metal or mixtures or alloys of these metals.Type: GrantFiled: February 9, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventor: Ernst W. Muller
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Patent number: 4760186Abstract: A process for the preparation of substituted aromatic amines comprising (1) contacting a primary aromatic amine with an oxidizing agent in a homogeneous solution containing water, an oxidizable water-miscible organic solvent and a base, and (2) reducing the solution with a reducing agent to produce the substituted aromatic amine.Type: GrantFiled: September 15, 1986Date of Patent: July 26, 1988Assignee: Monsanto CompanyInventor: A. John Solodar
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Patent number: 4454348Abstract: Diphenylamine is made by the reaction in the vapor phase of two moles of aniline with the consequent evolution of ammonia; surprisingly high yields and selectivities are obtained by maintaining a significant concentration of ammonia in the catalyst zone, preferably by using the ammonia as a carrier for the aniline.Type: GrantFiled: October 13, 1982Date of Patent: June 12, 1984Assignee: United States Steel CorporationInventors: John E. Aiken, Marvin C. Fields, Robert M. Stickel
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Patent number: 4316988Abstract: A series of new diphenylamines have small alkyl substituents on the amino nitrogen and are useful as intermediates for the preparation of rodenticidal diphenylamines. One phenyl ring has 2,4-dinitro-6-trifluoromethyl substitution, and the other is substituted with no more than one methyl or trifluoromethyl group. The invention is particularly directed to N-alkyl-2,4-dinitro-3'-6-bis(trifluoromethyl)diphenylamines, which are additionally useful as insecticides and arachnicides.Type: GrantFiled: December 24, 1980Date of Patent: February 23, 1982Assignee: Eli Lilly and CompanyInventors: Albert J. Clinton, deceased, George O. P. O'Doherty
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Patent number: 4265833Abstract: A process for the preparation of hydroxy-diphenylamines by condensation of dihydroxybenzene with an excess amount of primary aromatic amine in the presence of a catalytic amount of an acid at elevated temperature is described wherein the excess aromatic amine and, if appropriate, the reaction product is distilled off from the reaction mixture in the presence of a base.Type: GrantFiled: November 5, 1979Date of Patent: May 5, 1981Assignee: Bayer AktiengesellschaftInventors: Friedrich Werner, Heinz U. Blank
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Patent number: 4256669Abstract: A process for the preparation of diaryl para-phenylenediamines from a crude para-aminophenol solution such as obtained by the catalytic hydrogenation of nitrobenzene in an aqueous acid reaction medium. The process comprises contacting the para-aminophenol containing acidic solution, after neutralization with ammonia, with an aromatic amine selected from the group consisting of aniline, mixed toluidines, ortho-toluidine, mixed xylidines, and mixtures thereof under conditions whereby the aromatic amine extracts the para-aminophenol from the crude feed solution and is separated therefrom. The separated solution comprised essentially of the aromatic amine extractant, para-aminophenol, and minor amounts of impurities is then contacted with an alkylation catalyst to produce the diaryl para-phenylenediamines.Type: GrantFiled: November 8, 1978Date of Patent: March 17, 1981Assignee: Mallinckrodt, Inc.Inventors: Roland G. Benner, Paul D. Henson