Two Benzene Rings Bonded Directly To The Same Nitrogen Patents (Class 564/433)
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Patent number: 5712418Abstract: The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: ##STR1## or the acid fluoride salts thereof wherein BLK is an N-amino protecting groupAA is an amino acid residue andX is H or a protecting group useful,and the first amino and peptide have a free amino group and a blocked carboxy end.Type: GrantFiled: August 2, 1994Date of Patent: January 27, 1998Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Ayman Ahmed El-Faham
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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: 5679856Abstract: A process is described for preparing diphenylamines of the formula ##STR1## by oxybromination of a phenol ether compound using elemental bromine in the presence of hydrogen peroxide and of a catalyst to give a brominated phenol ether compound which is subsequently reacted with a formanilide compound to give the compound of the formula (1).The oxybromination reaction is a regioselective, environmentally friendly and cost-efffective method of preparing brominated aromatic compounds.The diphenylamines of the formula (1) are industrially useful intermediates for the production, for example of dyes, and in particular of color formers of the fluoran type for pressure- or heat-sensitive recording systems.Type: GrantFiled: February 13, 1996Date of Patent: October 21, 1997Assignee: Ciba-Geigy CorporationInventor: Frederic Brunner
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Patent number: 5672760Abstract: The present invention provides an ablatively photodecomposable polymer having a photoabsorber bound to the polymer (the "ablatively photodecomposable polymer") which does not phase separate, nor does it crystallize. The ablatively photodecomposable polymer provides even ablation, high resolution and in preferred embodiments, can withstand potassium permanganate etchant and ferric chloride etchant. The ablatively photodecomposable polymer is strippable, although it can remain on the substrate if desired. The ablatively photodecomposable polymer comprises a polymer to which a photoabsorber is bound, either covalently or ionically. The present invention is also directed to a process for forming a metal pattern on a substrate employing the ablatively photodecomposable polymer.Type: GrantFiled: April 9, 1996Date of Patent: September 30, 1997Assignee: International Business Machines CorporationInventors: Francis Charles Burns, William Weathers Fleming, Victor Yee-Way Lee, Randy William Snyder
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Patent number: 5663440Abstract: An object of the invention is to propose diamino compounds expressed by the following general formula (1) which are suitable to obtain a raw material, a polyimide resin, for a liquid crystal aligning film without any image sticking and with a high voltage holding ratio at from a low temperature to a high temperature as well as the preparation thereof: ##STR1##Type: GrantFiled: October 2, 1995Date of Patent: September 2, 1997Assignee: Chisso CorporationInventors: Toshiya Sawai, Seiji Oikawa, Masaaki Yazawa, Shizuo Murata, Masaharu Hayakawa, Etsuo Nakagawa, Shinichi Sawada
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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: 5648543Abstract: Disclosed is a process for producing a 4-nitrosodiphenylamine of the formula (2) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen atom, methyl group, ethyl group, cyclohexyl group, methoxy group, ethoxy group or chlorine or bromine atom, or a salt thereof, comprising treating a diphenylamine represented by the formula (1) ##STR2## wherein R.sub.1 and R.sub.2 are as defined above with (i) a mixture of nitrogen oxides, (ii) a hydrogen halide and (iii) an aliphatic alcohol, wherein the atomic ratio of oxygen to nitrogen of the mixture of nitrogen oxides is more than 1.0 and less than 2.0. This process produces 4-nitrosodiphenylamine of the formula (2) or a salt thereof conveniently and effectively, and is industrially advantageous.Type: GrantFiled: June 6, 1995Date of Patent: July 15, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tetsuo Murata, Hiroyuki Takagi, Yasumi Katayama
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Patent number: 5633407Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and 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. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.Type: GrantFiled: May 18, 1995Date of Patent: May 27, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5623088Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.Type: GrantFiled: May 10, 1995Date of Patent: April 22, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, James K. Bashkin
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Patent number: 5618979Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.Type: GrantFiled: May 18, 1995Date of Patent: April 8, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5608111Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.Type: GrantFiled: May 5, 1995Date of Patent: March 4, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, James M. Allman, James K. Bashkin, Roger K. Rains
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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: 5550291Abstract: Disclosed herein is a stereospecific synthesis amenable to the large scale preparation of a hydrochloric acid addition salt of a chlorohydrin of the formula ##STR1## wherein R.sup.1 and R.sup.2 are amino protective groups and R.sup.3 is an amino acid side chain or a protected amino acid side chain. The synthesis involves reacting an aldehyde of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined hereinbefore with (chloromethyl)lithium at -20.degree. C. or below and contacting the resulting diastereoisomeric mixture of lithium alcoholates with aqueous hydrochloric acid to obtain a separable mixture of the hydrochloric acid addition salts of the chlorohydrin and its corresponding hydroxy diastereoisomer. The hydrochloric acid addition salt of the chlorohydrin is transformed readily into corresponding optionally amino-protected aminoepoxides; for example, 3(S)-(tert-butyloxycarbonylamino)-l,2(S)-epoxy-4-phenyl-butane.Type: GrantFiled: May 4, 1995Date of Patent: August 27, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
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Patent number: 5545751Abstract: A process for the preparation of 4-methoxy-2,2',6-trimethyldiphenylamine, which comprises heating and reacting 2,6-dimethylcyclohexanone and 2-methyl-4-methoxyaniline in the presence of a dehydrogenation catalyst while removing the resultant hydrogen and water from the reaction system.Type: GrantFiled: December 14, 1994Date of Patent: August 13, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Chiyuki Kusuda, Masayuki Furuya, Masaru Wada, Yoshihiro Irizato, Hiroshi Naruse, Teruyuki Nagata
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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: 5489711Abstract: An oligomer from diarylamines is disclosed which has desirable antioxidant properties in lubricating oils which contain synthetic ester lubricants. The oligomer is desirable for use at higher temperatures where it has less volatility than simple diarylamines. The oligomer has substantial portions of monosubstituted diphenylamine repeat units which result in linear oligomers. Di and polysubstituted diphenylamines may optionally be present as repeat units. These di and polysubstituted diphenylamines generally react as monofunctional reactants in oligomerization and tend to reduce the number of repeat units in the average oligomer.Type: GrantFiled: December 20, 1994Date of Patent: February 6, 1996Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 5488180Abstract: This invention relates to complex hydrophobe compounds and to alkoxylation products, i.e., condensation reaction products of alkylene oxides and complex hydrophobe compounds having at least one active hydrogen. This invention also relates to alkoxylation products that have beneficial, narrow molecular weight ranges.Type: GrantFiled: May 29, 1992Date of Patent: January 30, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard D. Jenkins, David R. Bassett, Danny E. Smith, John N. Argyropoulos, James E. Loftus, Gregory D. Shay
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Patent number: 5475139Abstract: This invention provides a novel process for the preparation of substituted derivatives of diphenyl amine. The special feature of this novel process is that low cost and recoverable phenolic salts are used as catalysts for molecular rearrangement and aminolysis to obtain substituted derivatives of diphenyl amine in high yield.Type: GrantFiled: October 22, 1993Date of Patent: December 12, 1995Assignee: Yung Shin Pharm. Ind. Co., Ltd.Inventors: Fangchen Lee, Tsung-Chung Liu
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Patent number: 5453541Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.Type: GrantFiled: December 6, 1993Date of Patent: September 26, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, James K. Bashkin
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Patent number: 5449829Abstract: A diphenylamine with both the phenyl groups being substituted is prepared by reacting a phenol with ammonia in the presence of a hydrogen transfer catalyst and a cyclohexanone; or by converting a portion of the phenol to the cyclohexanone in the presence of a hydrogen transfer catalyst and under hydrogen pressure and then reacting the remaining portion of the phenol with ammonia in the presence of the cyclohexanone so converted and the hydrogen transfer catalyst. The diphenylamine can be obtained very efficiently.Type: GrantFiled: June 15, 1994Date of Patent: September 12, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Chiyuki Kusuda, Masaru Wada, Teruyuki Nagata
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Patent number: 5403958Abstract: Disclosed is an electrophotographic member containing as a charge transport material a fluorine-containing N,N,N',N'-tetraarylbenzidine derivative which is remarkably excellent in solubility in an organic solvent and/or a binder such as polycarbonate resin, etc., can show very excellent electrophotographic properties such as high sensitivity, low residual potential and high durability. Further, a fluorine-containing N,N,N',N'-tetraarylbenzidine derivative usable as a charge transport material, and a process for producing the same are disclosed. Furthermore, a fluorine-containing diarylamine usable for producing the fluorine-containing N,N,N',N'-tetraarylbenzidine derivative, and a process for producing the same are disclosed.Type: GrantFiled: April 30, 1993Date of Patent: April 4, 1995Assignee: Hitachi Chemical Co., Ltd.Inventors: Yoshii Morishita, Yasushi Sugimoto, Shigeru Hayashida, Hiroko Ishikawa, Yoshiaki Noda, Shigeru Murakami, Munehiro Sato, Yoshinori Saito, Naoji Kurata, Yoshio Sugita
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Patent number: 5387725Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.Type: GrantFiled: July 12, 1993Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
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Patent number: 5367095Abstract: Polyoxyalkylene polyamine or aromatic diamines or xylylenediamines are modified by them to the Michael reaction with an ethylenically unsaturated monomer having an electron-withdrawing group to convert the primary amino groups at least in part to a secondary amino group of the formula:--NH--CH.sub.2 --CH(R)--Ywherein R is a hydrogen atom or methyl, and Y is an electron-withdrawing group. The modified amines find use in the manufacture of plastics such as polyurea elastomers or polyurea RIM.Type: GrantFiled: September 4, 1992Date of Patent: November 22, 1994Assignee: Nippon Paint Company, Ltd.Inventors: Toshiyuki Ohshima, Hideo Ishibashi, Rie Tamura, Satoshi Yamamoto, Takaharu Izumo
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Patent number: 5364830Abstract: Pressure or heat sensitive record materials with color-former sublimation problems reduced or eliminated whilst not reducing the color forming capability per unit weight of color former by providing what are in effect dimers of vinyl carbinols, with the vinyl carbinol residues, linked through the aryl groups of a diaryl amine.Type: GrantFiled: March 19, 1993Date of Patent: November 15, 1994Assignee: The Wiggins Teape Group LimitedInventors: Ivan Sheiham, Margaret P. Templey
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Patent number: 5344987Abstract: Optionally substituted diphenylamines can be obtained by reacting optionally substituted anilines with optionally substituted cyclohexanones over a supported catalyst at 200.degree.-450.degree. C. and 0.1-20 bar, the supported catalyst containing one or more metals having a dehydrogenating action selected from the group Ru, Pd, Os, Ir, Pt, Fe, Co, Ni, Re, Mn, Cu, Ag, Cr and Ce.Type: GrantFiled: July 16, 1993Date of Patent: September 6, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Hans-Josef Buysch
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Patent number: 5321159Abstract: Disclosed is a method for decolorizing alkylated diarylamines, which have been made using aluminum chloride catalyst, by mixing and optionally heating the colored diarylamine with clay, then separating the decolorized diarylamine from the clay. Alternatively, the alkylated diarylamines, which have been made using aluminum chloride catalyst, may be decolorized by passing the diarylamines through a filter medium comprising clay.Type: GrantFiled: December 8, 1993Date of Patent: June 14, 1994Assignee: The B. F. Goodrich CompanyInventors: John T. Lai, Chong-Kuang Shaw, Deborah S. Filla
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Patent number: 5298661Abstract: Charge transporting materials having general formula (I): ##STR1## R.sup.1 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; an aralkyl group; a nitro group; an unsubstituted or substituted aryl group; a halogen; an amino group; an unsubstituted or substituted dialkylamino group; R.sup.2 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; or a halogen; R.sup.3 represents hydrogen; an alkyl group having 1 to 4 carbon atoms; an alkoxyl group having 1 to 4 carbon atoms; a halogen; a dialkylamino group; an amino group; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; a methylenedioxy group; an aralkyl group; or an unsubstituted or substituted aryl group; R.sup.Type: GrantFiled: June 18, 1993Date of Patent: March 29, 1994Assignee: Ricoh Company, Ltd.Inventors: Tomoyuki Shimada, Masaomi Sasaki, Tamotsu Aruga
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Patent number: 5213699Abstract: N-Allyl substituted p-phenylenediamine compounds are very effective antioxidant stabilizers for organic material subject to oxidative or thermal degradation, particularly for lubricant compositions.Type: GrantFiled: September 10, 1992Date of Patent: May 25, 1993Assignee: Ciba-Geigy CorporationInventors: Joseph E. Babiarz, Thelma Spivack
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Patent number: 5196592Abstract: Diphenylamine, which can be substituted by lower alkyl and/or lower alkoxy, is obtained from the corresponding N-cyclohexylidene-aniline by catalytic dehydrogenation, a rhodium-containing catalyst being employed.Type: GrantFiled: December 11, 1991Date of Patent: March 23, 1993Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Helmut Waldmann, Reinhard Langer, Gerhard Darsow, Hans-Josef Buysch
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Patent number: 5196606Abstract: A novel synthesis of aromatic tertiary amines involves reacting an aromatic anil and an aromatic ether in a molar ratio of 1:1; adjusting the ratio to 2:1 produces novel enamines and by employing a two step process for enamine production, various unsymmetrically substituted enamines can be obtained which are readily hydrolyzed to corresponding deoxybenzoins which in turn are readily oxidized to benzils, the aromatic tertiary amines may be used to produce charge transport layers in xerography, while the benzils may be used to produce a variety of desired polymers.Type: GrantFiled: November 26, 1991Date of Patent: March 23, 1993Inventors: Allan S. Hay, Martino Paventi
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Patent number: 5186852Abstract: A composition prepared by adding a p,p'-dinonyldiphenylamine represented by the following general formula: ##STR1## wherein R.sub.1 and R.sub.2 may be the same or different from each other and each stand for a branched alkyl group having 6 carbon atoms,and an N-p-alkylphenyl-.alpha.-naphthylamine represented by the following general formula: ##STR2## wherein R.sub.3 is an alkyl group having 12 to 15 carbon atoms derived from a propylene oligomer,as essential components to a mineral oil having an aromatic content of 30% by weight or below and/or a synthetic oil containing no aromatic ring in its structural unit.Type: GrantFiled: January 8, 1990Date of Patent: February 16, 1993Assignee: Nippon Oil Co., Ltd.Inventors: Noboru Ishida, Hiroyuki Takashima
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Patent number: 5167696Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.Type: GrantFiled: February 7, 1991Date of Patent: December 1, 1992Assignee: Imperial Chemical Industries PLCInventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
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Patent number: 5117063Abstract: A method of producing 4-ADPA is disclosed wherein aniline and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA. The 4-ADPA can be reductively alkylated to produce p-phenylenediamine products which are useful as antiozonants.Type: GrantFiled: June 21, 1991Date of Patent: May 26, 1992Assignee: Monsanto CompanyInventors: Michael K. Stern, James K. Bashkin
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Patent number: 5107024Abstract: Selective removal of primary amines from technical grade diphenylamine by contacting a solvent solution of said diphenylamine with a cationic exchange resin having sulfonic acid group functionality in the presence of up to about 3 percent water.Type: GrantFiled: May 22, 1991Date of Patent: April 21, 1992Assignee: Atochem Agri, S.A.Inventors: Pieter Kool, Eliezer L. Sigall, Samuel Meghir
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Patent number: 5082938Abstract: Enhanced branched chain hydroxyl compounds are provided of formulaY--(Z).sub.1-6wherein Y is the residue of a nucleophile devoid of conjugated divalent linking moieties, and each Z is a poly(oxyalkylene) moiety having a molecular weight of from about 200-10,000 and containing at least one glycidol residue, wherein at least one of the primary oxy sites of said glycidol residue is linked preferably directly to a first epoxide residue of three or more carbons, and wherein said first epoxide residue is linked through a secondary oxy site preferably directly to a second epoxide reside having a primary terminal hydroxyl.Type: GrantFiled: March 1, 1990Date of Patent: January 21, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, David J. Moody
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Patent number: 5081251Abstract: Stilbene compounds of the general formula Ia, Ib or IcR.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.3 R.sup.4 R.sup.5 R.sup.6 (Ia)R.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.2 R.sup.4 R.sup.5 R.sup.6 --CH.dbd.CH--Ar.sup.3 R.sup.7 R.sup.8 R.sup.9 (Ib)R.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.2 (CH.sub.2).sub.n Ar.sup.3 --CH.dbd.CH--Ar.sup.4 R.sup.4 R.sup.5 R.sup.6 (Ic)where Ar.sup.1 to Ar.sup.4 are identical or different aromatic or quasi-aromatic radicals and n is from 0 to 20 and where either at least one of the radicals R.sup.1 to R.sup.6 or R.sup.9 is hydrocarbon-solubilizing alkyl, alkoxy, dialkylamino or diarylamino of 4 or more carbon atoms in the alkyl moiety or, if formula Ic contains no radicals R.sup.1 to R.sup.6, n is not less than 4, are prepared by metalating a toluene/xylene analog R.sup.1 R.sup.2 R.sup.3 ArCH.sub.3 or H.sub.3 CR.sup.4 R.sup.5 R.sup.6 ArCH.sub.Type: GrantFiled: September 7, 1989Date of Patent: January 14, 1992Assignee: BASF AktiengesellschaftInventors: Dietmar Bender, Klaus Bronstert
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Patent number: 5047590Abstract: Compounds having formula (I), which are useful as starting or intermediate materials for preparing organic photoconductive materials, or as organic photoconductive materials: ##STR1## wherein R.sup.1 is a nitro group, an amino group or a diphenylamino group which may have a substituent; and R.sup.2 is hydrogen or an alkyl group having 1 to 6 carbon atoms, and methods of preparing the above compounds are disclosed.Type: GrantFiled: May 29, 1990Date of Patent: September 10, 1991Assignee: Ricoh Company, Ltd.Inventors: Tomoyuki Shimada, Masaomi Sasaki, Tamotsu Aruga
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Patent number: 4996362Abstract: 5-[(4-N,N-ditolylamino)benzyl]-5H-dibenzo[a,d]-cycloheptane derivatives having formula (I), which are useful as organic photoconductive materials in electrophotography.Type: GrantFiled: May 3, 1990Date of Patent: February 26, 1991Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tomotsu Aruga
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Patent number: 4992589Abstract: Compounds of the formula (1) ##STR1## in which X denotes a sulfur atom or the group ##STR2## in which R denotes a hydrogen atom, an alkylene-C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 - or alkyl-C.sub.1 -C.sub.6 - group, each of which can be substituted by hydroxyl, sulfo, carboxyl or cyano groups, R.sub.1 denotes a hydrogen atom or an alkyl-C.sub.1 -C.sub.6 -group which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), hydroxyl, amino, methylamino, acetylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino, methoxy, ethoxy, .beta.-hydroxyethylsulfonyl, phenyl, monosulfophenyl, disulfophenyl, or 4-[.beta.-hydroxyethylsulfonyl]-2-sulfophenyl groups, or represents a phenyl or naphthyl group, each of which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), alkyl-C.sub.1 -C.sub.4 -, alkoxy-C.sub.1 -C.sub.4 -, amino, methylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino or acetylamino groups, and R.sub.Type: GrantFiled: August 10, 1988Date of Patent: February 12, 1991Assignee: Hoechst AktiengesellschaftInventors: Hermann Fuchs, Theodor Papenfuhs, Werner Brodt, Folker Kohlhaas
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Patent number: 4990673Abstract: Process for the preparation of 4,4'-dinitrodiphenylamine which comprises reacting 1 mole of 4-halonitrobenzene with about 1 to about 3 moles of an alkali metal cyanate in the presence of about 0.5 to about 5 moles of water in dimethylsulfoxide at temperatures of about 150.degree. to about 170.degree. C.Type: GrantFiled: November 16, 1989Date of Patent: February 5, 1991Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Tronich, Peter Hess
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Patent number: 4973759Abstract: Alkylated aromatic amines can be isolated from crude catalyst-containing mixtures of these with olefins by a procedure in which in general equivalent amounts of an inorganic base and water are added to the alkylation mixture, the catalyst is hydrolysed, the water present in the reaction mixture after the hydrolysis is removed by distillation and the solid catalyst residue is separated off. The catalyst-free alkylation mixture which remains is then fed to customary further working up.Type: GrantFiled: September 20, 1989Date of Patent: November 27, 1990Assignee: Bayer AktiengesellschaftInventors: Alfons Klein, Helmut Fiege
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Patent number: 4957838Abstract: An electrophotographic photoconductor is disclosed, which comprises an electroconductive support and a photoconductive layer formed thereon comprising as an effective component at least one triphenylamine compound represented by the following formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a halogen, which may be the same or different. Further, novel triphenylamine compounds for use in the electrophotographic photoconductor are disclosed.Type: GrantFiled: September 29, 1989Date of Patent: September 18, 1990Assignee: Ricoh Company, Ltd.Inventors: Tamotsu Aruga, Masaomi Sasaki, Tomoyuki Shimada
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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: 4906662Abstract: Disclosed are phenol derivatives of the formula ##STR1## wherein R.sup.1 is a substituted phenyl group, R.sup.2 and R.sup.3 are C.sub.1 -C.sub.6 alkyl group and of the formula ##STR2## wherein R.sup.8, R.sup.9 and R.sup.10 are C.sub.1 -C.sub.6 alkyl and the like and A is H, C.sub.1 -C.sub.6 alkylsulfonyl and the like substituents. These compounds and some related compounds have anti-inflammatory activity and lipoxygenase inhibitory activity.Type: GrantFiled: January 27, 1987Date of Patent: March 6, 1990Assignee: Otsuka Pharmaceutical Factory, Inc.Inventors: Kinji Hashimoto, Kiyoto Goto, Ken-ichi Kanai, Yoshiaki Tsuda
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Patent number: 4879327Abstract: The invention relates to amine salts of phosphorous acid having a structure of the s-triazine, 1,2,4-triazole, benzimidazole, heptazine, pyrimidine, or piperazine type which may be combined with a polyhydroxylated compound as fireproofing agents for plastics, particularly polyamides and polyolefins, the process of fireproofing said plastics, and the resultant fireproofed plastics.Type: GrantFiled: March 31, 1988Date of Patent: November 7, 1989Assignee: AtochemInventors: Pierre Poisson, Nadine Rivas, Pierre Deloy
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Patent number: 4859206Abstract: This invention encompasses compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently are hydrogen, C.sub.1-4 alkyl, or C.sub.2-4 hydroxyalkyl; one of R.sup.3 to R.sup.7 is --SO.sub.3 H or --COOH; and the remaining of R.sup.3 to R.sup.7 independently are hydrogen, chlorine, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or --NR.sup.8 R.sup.9, where R.sup.8 and R.sup.9 independently are hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkoxy, or where --NR.sup.8 R.sup.9 is piperidine, morpholine, piperazine, or pyrrolidone; or a water soluble salt thereof; hair dye preparation containing these compounds, and methods for dyeing hair using such preparation.Type: GrantFiled: February 26, 1988Date of Patent: August 22, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: David Rose, Edgar Lieske, Horst Hoeffkes, Norbert Maak
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Patent number: 4859556Abstract: An electrophotographic photoconductor is disclosed which comprises an electroconductive support material and a photosensitive layer comprising at least one of the stilbene compounds of the formula ##STR1## wherein R.sup.1 represents hydrogen or ##STR2## R.sup.2 represents hydrogen, an alkyl group or a substituted or unsubstituted phenyl group; A represents ##STR3## when R.sup.1 is hydrogen; while, when R.sup.1 is ##STR4## A represents ##STR5## a 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, wherein R.sup.3 represents hydrogen, an alkyl group, an alkoxy group, a halogen or a substituted amino group represented by ##STR6## in which R.sup.4 and R.sup.5 independently represent an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, and R.sup.4 and R.sup.5 may form a ring in combination, and m is an integer of 0 through 3 and n is an integer of 0 or 1, provided that, when R.sup.1 is hydrogen and n=0, A is ##STR7## in which R.sup.Type: GrantFiled: August 9, 1988Date of Patent: August 22, 1989Assignee: Ricoh Company, Ltd.Inventor: Masaomi Sasaki
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Patent number: 4840971Abstract: An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.Type: GrantFiled: April 2, 1987Date of Patent: June 20, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano