Two Carbocyclic Rings, At Least One Of Which Is Benzene, Bonded Directly To The Same Nitrogen Patents (Class 564/431)
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Publication number: 20010033944Abstract: A light-emitting material which serves to emit light having a high brightness and is almost free of deterioration in light emission, and an organic EL device for which the light-emitting material is adapted, the material having the formula (1) disclosed in claim 1, 2 or 3.Type: ApplicationFiled: March 17, 1998Publication date: October 25, 2001Inventors: TOSHIKAZU ONIKUBO, MICHIKO TAMANO, SATOSHI OKUTSU, TOSHIO ENOKIDA
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Patent number: 6280859Abstract: A light-emitting material which serves to emit light having a high brightness and is almost free of deterioration in light emission, and an organic EL device for which the light-emitting material is adapted, the material having the formula [1],Type: GrantFiled: March 17, 1998Date of Patent: August 28, 2001Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Toshikazu Onikubo, Michiko Tamano, Satoshi Okutsu, Toshio Enokida
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Publication number: 20010008711Abstract: An organic light-emitting device comprising a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer formed between a pair of electrodes, wherein at least one layer comprises at least one kind of compound represented by the following formula (1): 1Type: ApplicationFiled: January 8, 2001Publication date: July 19, 2001Inventor: Tatsuya Igarashi
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Patent number: 6235736Abstract: A 3-anilino-2-cycloalkenone derivative of the formula (I): wherein, R1 represents a C1 to C8 alkyl group, which may have a substituent, except for a methyl group, a C3 to C7 cycloalkyl group, a 3-tetrahydrofuryl group, an 2-indanyl group, etc., R2 represents a C1 to C4 alkyl group, R3 represents a hydrogen atom, a C3 to C7 alkyl group, which may have a substituent, a C3 to C7 cycloalkyl group, etc., R4 represents a hydrogen atom, a C1 to C5 alkyl group, which may have a substituent, a halogen atom, etc., R5, R6, R7, and R8 independently represent a hydrogen atom, a C1 to C5 alkyl group, which may have a substituent, etc., X represents —(CR11R12)n—, wherein n is 0 to 2, R11 and R12 independently represent a hydrogen atom, a C1 to C5 alkyl group, which may have a substituent, etc.Type: GrantFiled: March 20, 2000Date of Patent: May 22, 2001Assignee: Nikken Chemicals Co., Ltd.Inventors: Shinji Ina, Kenjirou Yamana, Kyoji Noda, Akane Takahama, Toshihiko Akiyama
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Patent number: 6124503Abstract: A method of making an alkylaminoarylcarbonyl compound having Formula I: ##STR1## wherein R is an alkyl group;A is an aryl (including heteroaryl) ring;each R' is independently an alkyl group which may form a ring with Z or Z';p is 0, 1, 2, or 3;each Z, Z', and Y is independently hydrogen or a substituent; andn is 0, 1, or 2;comprising:(a) blocking the carbonyl function of an aminoarylcarbonyl compound via condensation with an active methylene compound(b) alkylating this blocked amniocarbonyl compound via reductive alkylation with an alkyl or aryl (including heteroaryl) carbonyl compound, and(c) deblocking of the blocked alkylaminoarylcarbonyl compound via base hydrolysis to regenerate the carbonyl function and give the desired alkylaminocarbonyl compound.Type: GrantFiled: December 31, 1998Date of Patent: September 26, 2000Assignee: Eastman Kodak CompanyInventors: Chang-Kyu Kim, Jared B. Mooberry, David Hoke, James J. Seifert
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Patent number: 6100430Abstract: An alicyclic polyamine of the formula (1) ##STR1## wherein Y.sub.1 represents a saturated aliphatic hydrocarbon group and R.sub.1 through R.sub.4 are the same or different and each represents hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group. The alicyclic polyamine can be obtained by subjecting a 3-formylcycloalkanone or 3-formylcycloalkenone to reductive amination reaction.Type: GrantFiled: September 10, 1998Date of Patent: August 8, 2000Assignee: Daicel Chemical Industries, Ltd.Inventors: Kenichi Yamamoto, Kazuyuki Matsuoka, Hiroshi Yagihara
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Patent number: 6080790Abstract: Compounds of formula (1) ##STR1## are described wherein Y represents a halogen atom or a group --OR.sup.1, where R.sup.1 is an optionally substituted alkyl group; R.sup.2 represents an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 is a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen or sulphur atoms or a group --N(R.sup.4)-- where R.sup.4 is a hydrogen atom or an alkyl group; X is --O--, --S--, or --N(R.sup.5)--, where R.sup.5 is a hydrogen or an alkyl group; with the proviso that when X is --O-- then R.sup.3 is not a 3-cyanamino-6-pyridazinyl or a 3-chloro-6-pyridazinyl group; and the salts, solvates, hydrates and N-oxides thereof.The compounds are selective and potent inhibitors of phosphodiesterase IV and are useful for the prophylaxis and treatment of inflammatory diseases and the alleviation of conditions associated with central nervous malfunction.Type: GrantFiled: May 30, 1997Date of Patent: June 27, 2000Assignee: Celltech Therapeutics, LimitedInventors: Ewan Campbell Boyd, Michael Anthony William Eaton, Graham John Warrellow
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Patent number: 5665756Abstract: Novel aminoalkyloximes of the formula ##STR1## wherein: a. X is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, or a group of the formula ##STR2## wherein Y is hydrogen or loweralkyl, and p is 1 or 2; b. A is a group of the formula ##STR3## c. R.sup.1 and R.sup.2 are independently hydrogen or lowerakyl; and d. m is 2 to 6 and n is 0, or 2 to 6, inclusive, serotonin reuptake inhibitors, useful for treating depression and obsessive compulsive disorders are described. Also described are precursors of and processes for the preparation of such aminoakyloximes.Type: GrantFiled: August 3, 1994Date of Patent: September 9, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
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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: 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: 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: 5468775Abstract: The present invention concerns enaminones having the formula: ##STR1## wherein R is from the group consisting of COOCH.sub.3 and COOC.sub.2 H.sub.5 ; R.sup.1 is from the group consisting of H and CH.sub.3 ; R.sup.2 is from the group consisting of H when R.sup.1 is CH.sub.3 and CH.sub.3 when R.sup.1 is H; and R.sup.3 is from the group of first radicals consisting of benzyl, phenethyl, disubstituted phenyl and trisubstituted phenyl. The substituted species are second radicals having positive lipophilicity selected from the group consisting of F, Cl, Br, and I.Type: GrantFiled: March 2, 1993Date of Patent: November 21, 1995Assignee: Howard UniversityInventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
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Patent number: 5403853Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independently, hydrogen, straight or branched chain alkyl or mono- or bi-cyclic alkyl;A is a substituted phenyl group containing one or two substituents selected from cyano, nitro, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, sulfamyl, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfone, perfluoroalkylsulfone, arylsulfone, chloro, bromo, fluoro, iodo, 1-imidazolyl or carboxyl; or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.Type: GrantFiled: June 13, 1994Date of Patent: April 4, 1995Assignee: American Home Products CorporationInventors: John A. Butera, Schuyler A. Antane
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Patent number: 5395971Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X--Y).Type: GrantFiled: March 11, 1994Date of Patent: March 7, 1995Assignee: The Board of Regents of The University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5371294Abstract: Cyclohexylamine and dicyclohexylamine can be prepared as a mixture with one another by reaction of phenol with aniline, ammonia or a mixture of aniline and ammonia in the presence of hydrogen over a catalyst, the reaction being carried out according to the invention over a palladium catalyst which has a support of niobic acid or tantalic acid or a mixture of niobic acid and tantalic acid or a support containing such acids. The reaction is carried out at 100.degree.-220.degree. C. under an H.sub.2 partial pressure of 0.5-500 bar.Type: GrantFiled: October 2, 1992Date of Patent: December 6, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Josef Buysch, Gerhard Darsow
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Patent number: 5349109Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).Type: GrantFiled: August 26, 1993Date of Patent: September 20, 1994Assignee: The Board of Regents of the University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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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: 5319143Abstract: There are disclosed certain bis(aminoethanethiols) and the salts thereof which find utility as intermediates in the preparation of certain dye-providing compounds useful in photographic imaging systems.Type: GrantFiled: July 31, 1992Date of Patent: June 7, 1994Assignee: Polaroid CorporationInventors: David Messersmith, David P. Waller
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Patent number: 5292957Abstract: A process for the preparation of N-alkylhalogenoanilines of the formula (I) 100.degree. ##STR1## in which X is a chlorine or bromine atom and n is the number 1 or 2, R.sup.1 is an alkyl (C.sub.1 -C.sub.4) radical, R.sup.2 an alkyl (C.sub.1 -C.sub.6) radical or R.sup.1 and R.sup.2 together with the carbon atom can form a five- or six-membered cycloalkane ring, by reacting a halogenonitrobenzene of the formula (II) ##STR2## in which X and n have the abovementioned meanings with an at least stoichiometric amount of a carbonyl compound of the formula (III) ##STR3## in which R.sup.1 and R.sup.2 have the meanings mentioned or R.sup.1 and R.sup.2 together with the carbon atom of the carbonyl group can form a five- or six-membered cycloalkane ring, in an inert organic solvent at temperatures of about 10 to about 100.degree. C., at a hydrogen superatmospheric pressure of about 0 to about 50 bar, in the presence of a platinum catalyst on activated carbon.Type: GrantFiled: February 20, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Werner Brodt, Theodor Papenfuhs
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Patent number: 5283248Abstract: The present invention relates to novel substituted pyrimidobenzimidazole derivatives of the formula ##STR1## wherein the substituents are as described in the specification, and pharmaceutically acceptable salts thereof.The products have an inhibitory action on the DNA-gyrase activity in bacteria. They can accordingly be used for the prevention or control of bacterial infections.Type: GrantFiled: June 25, 1992Date of Patent: February 1, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Christian Hubschwerlen, Ivan Kompis, Jean-Luc Specklin
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Patent number: 5252737Abstract: A process for preparing N-aliphatic substituted p-phenylenediamine intermediates is provided which comprises contacting an aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable solvent system, and reacting the aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable base and a controlled amount of protic material at a suitable temperature in a confined reaction zone. In one embodiment, the N-aliphatic substituted p-phenylenediamine intermediates are reduced to N-aliphatic substituted p-phenylenediamines and the N-aliphatic substituted p-phenylenediamines can be reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines. In another embodiment of the invention, N-aliphatic substituted p-phenylenediamine intermediates are reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines.Type: GrantFiled: May 22, 1992Date of Patent: October 12, 1993Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng
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Patent number: 5233091Abstract: This invention relates to a novel process for preparing novel N-cyclopropyl intermediates useful for preparing certain of the 1,7-disubstituted-6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives of this invention which contain a cyclopropyl substituent at the 1 position as well as other 1,4-dihydroquinol-4-one-3-carboxylic acid derivatives so substituted with cyclopropyl.Type: GrantFiled: May 29, 1991Date of Patent: August 3, 1993Assignee: Pfizer Inc.Inventor: Paul R. McGuirk
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Patent number: 5233089Abstract: A novel enamine derivative is effective as a charge transport material and can provide an electrophotographic plate excellent in sensitivity, photoresponse and durability.Type: GrantFiled: December 30, 1987Date of Patent: August 3, 1993Assignee: Hitachi, Ltd.Inventors: Yasuo Katsuya, Takayuki Akimoto, Yoshii Morishita, Yasushi Shinbo, Akira Kageyama, Shigeru Hayashida
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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: 5039682Abstract: This invention relates to novel 1,7-disubstituted-6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and certain esters and cation salts thereof. This invention further relates to preparation of the compounds, antibacterial compositions containing the compounds and methods of using the compounds.This invention also relates to a novel process for preparing novel N-cyclopropyl intermediates useful for preparing certain of the 1,7-disubstituted-6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives of this invention which contain a cyclopropyl substituent at the 1 position as well as other 1,4-dihydroquinol-4-one-3-carboxylic acid derivatives so substituted with cyclopropyl.Type: GrantFiled: June 21, 1988Date of Patent: August 13, 1991Assignee: Pfizer Inc.Inventor: Paul R. McGuirk
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Patent number: 5011939Abstract: A hydroxy arylamine compound is disclosed represented by the formula: ##STR1## wherein: m is 0 or 1,Z is selected from the group consisting of: ##STR2## n is 0 or 1, Ar is selected from the group consisting of: ##STR3## R is selected from the group consisting of --CH.sub.3, --CH.sub.2 H.sub.5, --C.sub.3 H.sub.7, and --C.sub.4 H.sub.9,Ar' is selected from the group consisting of: ##STR4## X is selected from the group consisting of: ##STR5## s is 0, 1 or 2, the dihydroxy arylamine compound being free of any direct conjugation between the --OH groups and the nearest nitrogen atom through one or more aromatic rings. The dihydroxy arylamine compound may be employed in an electrophotographic imaging member and the member may be used in an electrophotographic imaging process.Type: GrantFiled: May 23, 1989Date of Patent: April 30, 1991Assignee: Xerox CorporationInventors: William W. Limburg, John F. Yanus, Dale S. Renfer, Richard L. Schank, Beng S. Ong
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Patent number: 4978787Abstract: 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: GrantFiled: September 11, 1989Date of Patent: December 18, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
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Patent number: 4948794Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, C.sup.1 or Br when R.sup.1 is CH.sub.3 ; orR.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; orR.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl; orR.sup.7 and R.sup.Type: GrantFiled: November 8, 1988Date of Patent: August 14, 1990Assignee: A/S FerrosanInventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
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Patent number: 4812543Abstract: A novel metathesis catalyst polymerizable composition is provided which comprises at least one ring-opening metathesis catalyst polymerizable norbornene-type monomer and at least one ring-opening metathesis catalyst polymerizable amine antioxidant comonomer.Type: GrantFiled: March 1, 1988Date of Patent: March 14, 1989Assignee: Hercules IncorporatedInventors: Albert S. Matlack, Martin J. Paisner
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Patent number: 4764534Abstract: 4-Substituted-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1-naphthalenamine derivatives, useful as anticoccidial agents both alone and in combination with polyether antibiotics.Type: GrantFiled: July 17, 1984Date of Patent: August 16, 1988Assignee: Eli Lilly and CompanyInventors: Albert J. Clinton, deceased, George O. P. O'Doherty
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Patent number: 4724267Abstract: Bis(haloacylaromatic) compounds have been made by a new process in which monohaloacylated aromatic compounds have been reacted by a coupling reaction. These bis(haloacylaromatic) compounds can be employed as monomers in the preparation of polyesters and polyamides which have easy processability. The monohaloacylated compound is coupled by reacting two moles of the monomer with a carbon or sulfur compound containing at least two halogen atoms in the presence of a Friedel-Crafts catalyst.Type: GrantFiled: May 23, 1986Date of Patent: February 9, 1988Assignee: The Dow Chemical CompanyInventors: George M. St. George, Marlin E. Walters
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Ether compound, and an insecticidal and acaricidal composition containing it as an active ingredient
Patent number: 4664698Abstract: An ether compound represented by the following general formula (I), its production method and an insecticidal and acaricidal composition containing as an active ingredient: ##STR1## wherein X represents an oxygen atom or a group represented by the formula --NH--; when X represents an oxygen atom, Z represents a nitrogen atom or a group represented by the formula --CH.dbd.; when X represents --NH--, Z represents --CH.dbd.; when X represents an oxygen atom and Z represents a nitrogen atom, or when X represents --NH--, R.sub.1 represents a hydrogen or fluorine atom; when X represents an oxygen atom and Z represents --CH.dbd., R.sub.1 represents a fluorine atom; Y.sub.1 and Y.sub.2, which may be identical or different, represent a hydrogen or halogen atom or an alkyl, haloalkyl, alkoxyl or haloalkoxyl group; m and n represent an integer of 1 to 4 and the sum of them is not more than 5; R.sub.2 represents a methyl group or a chlorine atom; and R.sub.3 represents a methyl group, a halogen atom or a methoxy group.Type: GrantFiled: September 9, 1985Date of Patent: May 12, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano -
Patent number: 4591359Abstract: Acid nitrodyestuffs are prepared by treating aminonitrodiphenylaminesulfonic acids with an oxidizing agent in an aqueous medium, the oxidizing agent being hypochlorous acid or its alkali metal or alkaline earth metal salts and the reaction taking place at above pH 4 and at a temperature between 0.degree. and 100.degree. C. The dyestuffs thus obtainable dye even fresh full chrome grained leather in deep shades.Type: GrantFiled: August 23, 1984Date of Patent: May 27, 1986Assignee: Hoechst AktiengesellschaftInventor: Hasso Hertel
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Patent number: 4423065Abstract: Substituted-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]naphthalenamine derivatives useful as insecticides and ectoparasiticides.Type: GrantFiled: May 4, 1982Date of Patent: December 27, 1983Assignee: Eli Lilly and CompanyInventors: Albert J. Clinton, deceased, George O. P. O'Doherty
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Patent number: 4374291Abstract: Bis(ethynylphenyl) compounds are prepared by an improved synthesis process which increases yield and is suitable for large scale synthesis operations. Aromatic dianilines are diazotized to form aromatic halides that are subsequently coupled with an end-protecting group having acetylenic moieties. The end-protecting groups are subsequently removed leaving the desired diethynyl derivative in quantitative yields.Type: GrantFiled: November 6, 1981Date of Patent: February 15, 1983Assignee: Hughes Aircraft CompanyInventor: Kreisler S. Y. Lau
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Patent number: 4362893Abstract: C-Nitrosodiarylamines may be prepared in a single stage from diarylamines by adding alcoholic solutions of a hydrogen halide below the surface of a stirred mixture of the diphenylamine in an organic liquid containing water. The amount of water contained is critical, and amounts from about 1 to about 3 g per mole of diarylamine are preferred.Type: GrantFiled: June 3, 1981Date of Patent: December 7, 1982Assignee: UOP Inc.Inventor: Paul R. Kurek
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Patent number: 4287336Abstract: Chromogenic compounds of the formula ##STR1## wherein each of Y.sub.1 and Y.sub.2 independently represents an amino-substituted phenyl radical of the formula ##STR2## a 3-indolyl radical of the formula ##STR3## or a 3-carbazolyl radical of the formula ##STR4## and Q represents alkyl of 1 to 12 carbon atoms or unsubstituted or substituted aryl or aralkyl, while each of X.sub.1 and X.sub.2 independently represents hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents cycloalkyl, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl or lower alkoxy, or X.sub.1 and X.sub.2 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical, X.sub.3 represents hydrogen, halogen, nitro, lower alkyl or lower alkoxy, each of R and Z.sub.Type: GrantFiled: September 10, 1979Date of Patent: September 1, 1981Assignee: Ciba-Geigy CorporationInventor: Jean C. Petitpierre
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Patent number: 4268458Abstract: In a process for the preparation of an N-alkylated aromatic amine by contacting an aromatic amine with an aliphatic or cycloaliphatic alcohol at an elevated temperature and under increased pressure, in the presence of catalysts, the improvement wherein the reaction is carried out in the presence of a phosphorus oxyhalide.Type: GrantFiled: April 16, 1980Date of Patent: May 19, 1981Assignee: Bayer AktiengesellschaftInventors: Werner Schulte-Huermann, Heinz P. Hemmerich