Two Benzene Rings Bonded Directly To The Same Oxygen, Sulfur, Or Polysulfide Chain Patents (Class 564/430)
-
Patent number: 4694105Abstract: Herbicidal and plant growth regulating 3-alkoxyamino- and 3-polyalkoxyamino-2'-chloro-4-nitro-4'-trifluoromethyldiphenyl ethers of formula I ##STR1## wherein each of A, A', A" and A'" is an identical or different C.sub.1 -C.sub.4 alkylene radical which may be straight chain or branched; n is a value from 1 to 5; each of n', n" and n'" is zero or a value from 1 to 5; R is a C.sub.1 -C.sub.4 alkyl radical or a C.sub.1 -C.sub.4 alkylcarbonyl radical, which alkyl radicals may be substituted by halogen or cyano, or is a benzoyl or phenylsulfonyl radical which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or nitro, or, if A-O is not oxyethylene and/or if the sum of n+n'+n"+n'" is greater than 1, R is also hydrogen; R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.1 -C.sub.4 alkylcarbonyl or C.sub.1 -C.sub.4 haloalkylcarbonyl, which radicals R and R.sub.Type: GrantFiled: December 10, 1984Date of Patent: September 15, 1987Assignee: Ciba-Geigy CorporationInventor: Dieter Durr
-
Patent number: 4692554Abstract: A process for producing 1,3-bis(3-aminophenoxy)-benzenes which are very useful as a monomer for heat-resistant high molecular weight polymers is provided, which process comprises dehalogenating a bis(3-aminophenoxy)-halogenobenzene by its reduction, which compound is selected from the group consisting of 1,3-bis(3-aminophenoxy)-5-halogenobenzenes, 1,3-bis(3-aminophenoxy)-2,4-dihalogenobenzenes and 1,5-bis(3-aminophenoxy)-2,4-dihalogenobenzenes, these raw material compounds being respectively obtained by reacting a 1,3,5-trihalogenobenzene, a 1,2,3,4-tetrahalogenobenzene or a 1,2,4,5-tetrahalogenobenzene with 3-aminophenol in the presence of a dehydrohalogenating agent.Type: GrantFiled: August 7, 1984Date of Patent: September 8, 1987Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Keizaburo Yamaguchi, Yukihiro Yoshikawa, Yoshimitsu Tanabe, Kenichi Sugimoto, Akihiro Yamaguchi
-
Patent number: 4683333Abstract: Substituted bis-ethers, such as .alpha.,107 -bis-(4-aminophenoxy)-alkyls, are prepared in process which involves sequential addition of reactants, reagents or neutralizing compounds without recovery of intermediate products such as diamides and diamine acid salts. When water is used as the solvent, the process is simplified and product yields in excess of about 70% are obtained.Type: GrantFiled: November 22, 1985Date of Patent: July 28, 1987Assignee: The Dow Chemical CompanyInventors: Thomas R. Britt, Willie C. Burton
-
Patent number: 4670597Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic monoamine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide, in the presence of hydrogen iodide, ammonium iodide, or cuprous iodide.Type: GrantFiled: November 8, 1985Date of Patent: June 2, 1987Assignee: Ethyl CorporationInventors: Paul F. Ranken, Robert L. Davis
-
Patent number: 4670598Abstract: (Hydrocarbylthio)aromatic polyamines are prepared by reacting an aromatic polyamine, such as a diaminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide, in the presence of an iodide or bromide of a metal other than an alkali metal as a catalyst.Type: GrantFiled: November 8, 1985Date of Patent: June 2, 1987Assignee: Ethyl CorporationInventor: Robert L. Davis
-
Patent number: 4665000Abstract: Disclosed for incorporation in imaging members are novel aromatic ether compositions of the formula R--X--R.sub.1, wherein R and R.sub.1 are independently selected from arylamino and substituted arylamino groups, and X is selected from the group consisting of oxygen, sulfur, selenium, and tellurium. Also disclosed are photoresponsive imaging devices containing a photogenerating layer and in contact therewith a hole transport layer comprised of the aromatic ethers illustrated herein.Type: GrantFiled: October 19, 1984Date of Patent: May 12, 1987Assignee: Xerox CorporationInventors: Emery G. Tokoli, Anthony M. Horgan
-
Patent number: 4662935Abstract: Compounds of the formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group, or a cyano group,Y is a hydrogen atom, a halogen atom, or a trihalomethyl group, andZ is a substituted alkoxy group,and compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: September 16, 1981Date of Patent: May 5, 1987Assignee: Rohm and Haas CompanyInventors: Horst O. Bayer, Colin Swithenbank, Roy Y. Yih
-
Patent number: 4663484Abstract: New diaminoalkyldiphenyl ethers of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and denote hydrogen or methyl, but R.sup.1 and R.sup.2 do not simultaneously represent methyl,are prepared by a process wherein alkyldiphenyl ethers of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the above-mentioned meaning are acetylated, the diacetyl compounds obtained, in aqueous-alcoholic solution or suspension, are converted to the corresponding dioximes with hydroxylamine, the dried dioximes are subjected to a Beckmann rearrangement and thereafter the diacetylaminoalkyldiphenyl ethers formed are hydrolyzed by means of aqueous mineral acids or alkali metal hydroxide solutions to give the diamines.The new diaminoalkyldiphenyl ethers are used in the preparation of dyestuffs and polyurethanes and serve as monomers for the preparation of polymers.Type: GrantFiled: November 25, 1985Date of Patent: May 5, 1987Assignee: Bayer AktiengesellschaftInventor: Walter Horstmann
-
Patent number: 4663483Abstract: The synthesis and characterization of several polyenamine ketones are discussed wherein conjugated diacetylenic diketones and aromatic diamines are used as a route to the formation of high molecular weight polyenamine ketones which exhibit good mechanical properties and can be cast into creasible films. Typical polymerization conditions involved the reaction of stoichiometric amounts of 1,4- or 1,3-PPPO and a diamine at 60.degree.-130.degree. C. in m-cresol at (w/w) solids content of 8-26% for a specified period of time under a nitrogen atmosphere. Novel polyenamine ketones were prepared with inherent viscosities as high as 1.99 dl/g and tough, clear amber films with tensile strengths of 12,400 psi and tensile moduli of 397,000 psi were cast from solutions of the polymers in chloroform. The polymers exhibited T.sub.g s as high as 235.degree. C. and weight losses of 14% after aging at 232.degree. C. in circulating air for sixty hours.Type: GrantFiled: May 15, 1985Date of Patent: May 5, 1987Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Paul M. Hergenrother, Robert G. Bass, Mark S. Sinsky, John W. Connell
-
Patent number: 4650905Abstract: Diphenyl ethers of the formula ##STR1## where Z.sup.1 is hydrogen or halogen, Z.sup.2 is halogen, R.sup.1, R.sup.2 and R.sup.3 are each hydrogen or alkyl, R.sup.4 is alkyl or an araliphatic radical and n is a number from 1 to 8, are used for controlling undesirable plant growth.Type: GrantFiled: September 11, 1985Date of Patent: March 17, 1987Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Gerhard Hamprecht, Bruno Wuerzer
-
Patent number: 4633016Abstract: Compounds corresponding to the general formula ##STR1## wherein R.sup.3 represents H, CH.sub.3R.sup.4 represents H, C.sub.1-12 alkyl, C.sub.1-4 alkoxy, C.sub.1-12 alkylamino, C.sub.7-8 aralkylamino, arylamino, or C.sub.7-20 aralkyl,A represents a two-bonded group having the structure ##STR2## X may represent a single bond or --CO-- if it is attached to a carbon atom but only --CO-- if it is attached to a hetero atom,R.sup.1 represents R.sup.2, H or C.sub.1-4 alkyl,m represents 1 or 2 andn represents an integer from 1 to 12 are suitable as age resisters which can be built into polymers, in particular nitrile rubber.Type: GrantFiled: August 6, 1985Date of Patent: December 30, 1986Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Josef Witt, Zsolt Szentivanyi
-
Patent number: 4613619Abstract: The invention concerns novel anti-arrhythmic amino-alcohol derivatives, characterized by the general formula (1) ##STR1## or pharmaceutically acceptable salts thereof, wherein R.sub.1, R.sub.2 and R.sub.3 each independently represent hydrogen, alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms, acyloxy having 1-6 carbon atoms, hydroxy, halogen or optionally alkyl-substituted amino;R.sub.4 represents hydrogen, hydroxy or alkyl having 1-6 carbon atoms,R.sub.5 represents hydrogen or alkyl having 1-6 carbon atoms,R.sub.6 represents hydrogen, acyl having 1-18 carbon atoms or alkyl having 1-6 carbon atoms,R.sub.7 and R.sub.8 each independently represent hydrogen or alkyl having 1-6 carbon atoms,X represents a direct bond or an oxygen atom, andn and m each independently are integers having a value of 1 or 2, whereby the sum of n and m is 2 or 3.Type: GrantFiled: February 22, 1985Date of Patent: September 23, 1986Assignee: AKZO N.V.Inventors: Thomas Sleigh, David S. Savage, John K. Clark
-
Patent number: 4603222Abstract: Diphenyl ethers of the formula ##STR1## wherein m is 1-3, n is 1 or 2, R is hydrogen, carboxy, carboxylate salt or ester, formyl oxime, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride of the formula ##STR2## wherein m and n are as defined above with a nitro-phenoxide of the formula ##STR3## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.Type: GrantFiled: August 30, 1984Date of Patent: July 29, 1986Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
-
Patent number: 4594453Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide. The reaction is preferably conducted in the presence of a Lewis acid catalyst, such as aluminum chloride.Type: GrantFiled: June 11, 1984Date of Patent: June 10, 1986Assignee: Ethyl CorporationInventors: Paul F. Ranken, Bonnie G. McKinnie
-
Patent number: 4576857Abstract: Melt-fusible polyimides based on pyromellitic dianhydride and at least one defined aromatic diamine are useful in making low-void composites and thermoplastic tapes, which can be fabricated into articles such as, for example, aircraft and autobody panels, printed circuit boards, etc. Some of these polyimides are melt-processible and can be fabricated by conventional procedures such as extrusion and injection molding.Type: GrantFiled: September 21, 1983Date of Patent: March 18, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas P. Gannett, Hugh H. Gibbs
-
Patent number: 4566900Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1, Y, A, Z and n have the meanings given in the description, are used for controlling undesirable plant growth.Type: GrantFiled: December 1, 1982Date of Patent: January 28, 1986Assignee: BASF AktiengesellschaftInventors: Peter Plath, Ulrich Schirmer, Gernot Reissenweber, Bruno Wuerzer, Guenter Retzlaff
-
Patent number: 4566876Abstract: 2-Equivalent oxidative hair dye coupler compounds of the formula (I) ##STR1## wherein X is halogen or OR', wherein R and R' may be the same or different and represent alkyl, mono- or poly-hydroxyalkyl, alkoxyalkyl, alkylphenyl, aminoalkyl, mono- and di-alkylaminoalkyl, phenyl or phenylalkyl except that R and R' are not both methyl, and the acid addition salts thereof are used in oxidative hair dye compositions with conventional para bases. The amount of oxidizing agent can be reduced relative to similar compositions containing 4-equivalent meta coupler compounds. Some of the compounds of formula (I) in which X is OR' are novel compounds as is the elimination of HOR' during the oxidative coupling reaction.Type: GrantFiled: March 10, 1983Date of Patent: January 28, 1986Assignee: Clairol IncorporatedInventors: Keith C. Brown, John F. Corbett
-
Patent number: 4551551Abstract: Bis(aminophenyl) ethers are prepared by effecting condensation reaction of an (N-acetyl)aminophenol or the corresponding sodium or potassium (N-acetyl)aminophenate with a halonitrobenzene under condensation reaction conditions to form an (N-acetyl)aminophenylnitrophenyl ether and hydrogenating the nitro group thereof under nitro- group hydrogenation conditions to form an (N-acetyl)bis(aminophenyl) ether. The latter compound is hydrolyzed with aqueous mineral acid under acid hydrolysis conditions to form an acidic aqueous dispersion of the bis(aminophenyl) ether product, which can readily be recovered from the disperson. Final bis(aminophenyl) ether products thus prepared are typically of high purity and excellent color properties, i.e., substantially colorless.Type: GrantFiled: September 27, 1982Date of Patent: November 5, 1985Assignee: Mallinckrodt, Inc.Inventor: Ervin B. Inskip
-
Patent number: 4548976Abstract: Bis-(norbornyl or substituted norbornyl) derivatives of a phenol or phenylamine of the following formula: ##STR1## wherein each A is O or NH; M is a bivalent radical such as the residue of an aldehyde, ammonia, water or H.sub.2 S; each R is a hydrocarbyl or an inertly substituted hydrocarbyl group; each R.sub.1 is independently a hydrocarbyl or an inertly substituted hydrocarbyl group and each n is independently an integer from 0 to 3 are useful as antioxidants for a variety of materials including latex compositions for preparing latex foam backed carpets.Type: GrantFiled: May 18, 1984Date of Patent: October 22, 1985Assignee: The Dow Chemical CompanyInventors: Pierre DeRoche, Neil V. Kirby
-
Patent number: 4539428Abstract: Diaminodiphenyl ethers (DADPE's) are prepared by refluxing sodium or potassium aminophenate with chloronitrobenzene in dimethylformamide. The reaction mixture is hydrogenated directly without isolating the resulting intermediate product, aminophenyl-nitrophenyl ether, to form the corresponding DADPE, e.g., oxydianiline (ODA). The DADPE is crystallized from the hydrogenated reaction mixture in the presence of an aliphatic alcohol, which may be added to the reaction mixture prior to, during, or after hydrogenation. The resulting crystallized DADPE is typically of high purity and excellent color.Type: GrantFiled: May 10, 1982Date of Patent: September 3, 1985Assignee: Mallinckrodt, Inc.Inventors: Philip H. Merrell, Michael F. Ellis
-
Patent number: 4526608Abstract: Substituted phenoxyphenylhydroxyamines and pyridyloxyphenylhydroxyamines, and the use thereof for the control of weeds.Type: GrantFiled: March 31, 1983Date of Patent: July 2, 1985Assignee: Zoecon CorporationInventor: Shy-Fuh Lee
-
Patent number: 4521623Abstract: There are provided the aromatic diamines 2,2-bis-[(2-halo-4-aminophenoxy)-phenyl]hexafluoropropane, where the attached ortho halogen is preferably chlorine, and 4,4'-bis(4-aminophenoxy)biphenyl, as novel monomers for polyimide polymerizations. The former, when reacted with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, provides a polyimide having exceptional high-temperature performance. The latter diamine is a low-cost monomer for polyimide production.Type: GrantFiled: February 17, 1984Date of Patent: June 4, 1985Assignee: TRW Inc.Inventors: Robert J. Jones, Glenn E. C. Chang
-
Patent number: 4514574Abstract: Separate isomers via supercritical gas extraction.Type: GrantFiled: January 9, 1984Date of Patent: April 30, 1985Assignee: The Dow Chemical CompanyInventors: Kimio Inoue, Gale G. Hoyer, Stanley I. Bates
-
Patent number: 4506100Abstract: Novel polyimides, optionally end-capped with polymerizable or inert groups, and the polyamic acid or ester intermediates thereof are prepared by reacting a tetracarboxylic acid compound (e.g. pyromellitic dianhydride or 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride or its methyl diester) with diamines having the general formula ##STR1## wherein Z is oxygen or sulfur, X and/or Y are carbonyl or carbinol groups, the amine groups may be in the 2-, 3-, and/or 4-position, and isomerism is present when X and/or Y is a carbinol group. The polyimides may be end-capped by reaction, during or after their formation, with polymerizable groups such as 3-aminophenyl acetylene or 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride. The diamines are novel classes of amines when Z is sulfur and X and/or Y are carbonyl or carbinol groups and when Z is oxygen and X, Y, or X and Y are carbinol groups.Type: GrantFiled: August 4, 1982Date of Patent: March 19, 1985Assignee: National Starch and Chemical CorporationInventors: Jules E. Schoenberg, Stephen P. Anderson
-
Patent number: 4469893Abstract: Diphenyl esters of the formula ##STR1## wherein R is hydrogen, carboxy, carboxylate salt or ester, formyl, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride with a nitro-phenoxide of the formula ##STR2## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.Type: GrantFiled: March 22, 1982Date of Patent: September 4, 1984Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
-
Patent number: 4454350Abstract: A process for the acylation of halo- or trihalomethylbenzenes, wherein a halo- or trihalomethylbenzene is reacted with a carboxylic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: June 12, 1984Assignee: Rhone-Poulenc Specialities ChimiquesInventor: Michel Desbois
-
Patent number: 4401461Abstract: This invention relates to novel herbicidal compounds of the formula ##STR1## wherein X is a (C.sub.1 -C.sub.6)alkoxy group, a (C.sub.1 -C.sub.4)alkyl group, an alkoxyalkoxy group, wherein each alkyl moiety has 1 to 4 carbon atoms, a (C.sub.1 -C.sub.4)alkylamino group, a (C.sub.1 -C.sub.4)dialkylamino group, a halogen atom, a cyano group, a trifluoromethyl group, a hydroxy group, or a (C.sub.1 -C.sub.4) alkylthio group, andY is a hydrogen atom, or a halogen atom,to herbicidal compositions which contain these compounds, and to methods of controlling weeds with the herbicidal compositions.Type: GrantFiled: March 16, 1978Date of Patent: August 30, 1983Assignee: Rohm and Haas CompanyInventors: Harold F. Wilson, Marvin H. Fleischfresser
-
Patent number: 4393079Abstract: Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms or phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of formula I above are also novel.Type: GrantFiled: December 15, 1976Date of Patent: July 12, 1983Assignee: Beecham Group LimitedInventors: William G. Cole, Alexander C. Goudie, Carl J. Rose
-
Patent number: 4378298Abstract: Imines of 2,4'-diaminodiphenyl ethers are effective antioxidants in petroleum and petroleum-related products. Especially desirable are 2,4'-bis-(N,N'-arylmethylideneamino)phenyl ethers, where the aryl moiety is a heteroaromatic group.Type: GrantFiled: May 12, 1981Date of Patent: March 29, 1983Assignee: UOP Inc.Inventor: John T. Roberts
-
Patent number: 4377532Abstract: The invention relates to 3-phenoxybenzyl compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl and R.sub.2 is alkenyl or alkynyl, as intermediates for the production of biocides.The preparation of the 3-phenoxybenzaldehydes employed as intermediates is described. Novel 3-phenoxybenzaldehydes used as starting materials and the production thereof are also disclosed.Type: GrantFiled: February 19, 1982Date of Patent: March 22, 1983Assignee: Ciba-Geigy CorporationInventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
-
Patent number: 4375562Abstract: Process for the preparation of a bis-(amino-phenyl)-disulphide of the formula ##STR1## in which R represents hydrogen or halogen,which comprises contacting an amino-thiophenol of the formula ##STR2## or a salt thereof in which R has the abovementioned meaningwith sulphur or a sulphur-donating substance in an aqueous dispersion at a temperature of 10.degree. to 120.degree. C. and a pH value of 3 to 9.Type: GrantFiled: February 26, 1981Date of Patent: March 1, 1983Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Theodor Pfister, Rolf Putter
-
Patent number: 4370501Abstract: A simplified process for converting bis-phenols to dianilines is disclosed. Selected catalytic complexes are used to cause a nucleophilic displacement reaction between a bis-phenol and a quinazoline to occur thereby yielding a bis-quinazoline that may be subsequently converted into a bis-quinazolinone and hydrolyzed to form the desired dianiline.Type: GrantFiled: October 5, 1981Date of Patent: January 25, 1983Assignee: Hughes Aircraft CompanyInventor: Kreisler S. Y. Lau
-
Patent number: 4364875Abstract: The method of preparing a compound of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl of 1 to 8 carbon atoms, trifluoromethyl or acetyl;n is 1 when R.sub.1 has all the defined meanings, or 2 or 3 when R.sub.1 is halogen or alkyl;R.sub.2 is hydrogen; alkyl of 1 to 16 carbon atoms; alkenyl of 2 to 16 carbon atoms; alkinyl of 2 to 16 carbon atoms; monosubstituted alkyl of 2 to 6 carbon atoms, where the substituent is hydroxyl, alkoxy of 1 to 4 carbon atoms, phenoxy, halo-phenoxy, (alkyl of 1 to 4 carbon atoms) phenoxy, (alkoxy of 1 to 4 carbon atoms)phenoxy, nitro-phenoxy, cyano-phenoxy, amino or (alkyl of 1 to 4 carbon atoms)thio; benzyl; halo-benzyl; --NR.sub.3 R.sub.4 ; --CHR.sub.3 --COOR.sub.4 ; or --CHR.sub.3 --CONR.sub.4 R.sub.5, whereR.sub.3, R.sub.4 and R.sub.5 are each hydrogen or alkyl of 1 to 8 carbon atoms; andX.sub.1 and X.sub.2 are each hydrogen or halogen,which comprises reacting a compound of the formula ##STR2## wherein n, R.sub.1, X.sub.1 and X.sub.Type: GrantFiled: July 7, 1981Date of Patent: December 21, 1982Assignee: Celamerck GmbH & Co. KGInventors: Richard Sehring, Wolfgang Buck
-
Patent number: 4360375Abstract: A herbicidal composition which comprises a phenoxyphenoxy unsaturated derivative having the formula: ##STR1## wherein X represents a halogen atom or CF.sub.3 ; Y represents a hydrogen atom or a halogen atom; and Z represents --COOR, --COR", --COOH, --CH.sub.2 OH, or --CH.sub.2 OR"'.Type: GrantFiled: December 23, 1980Date of Patent: November 23, 1982Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
-
Patent number: 4358308Abstract: The 4-perfluoroacetyl-, 4-perfluoromethylthio-, 4-perfluoromethylsulfinyl-, and 4-perfluoromethylsulfonyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: October 19, 1981Date of Patent: November 9, 1982Assignee: Rohm and Haas CompanyInventor: Colin Swithenbank
-
Patent number: 4356325Abstract: Acetylene terminated sulfones and oligomers thereof are prepared by reacting a sulfonyldiphenol with a material selected from the group consisting of a meta-dibromobenzene, a para-dibromobenzene and mixtures thereof in the presence of a potassium base to form a bis-bromophenoxydiphenyl sulfone, which is reacted with a substituted terminal acetylene compound containing at least three carbon atoms and an hydroxy group on the carbon atom adjacent to the acetylene group to form an hydroxy-acetylene terminated phenoxydiphenyl sulfone, which is then subjected to base catalyzed cleavage to form the desired acetylene terminated sulfones and oligomers. An hydroxy-arylacetylene terminated sulfone is prepared by reacting a sulfonyldiphenyl with a material selected from the group consisting of meta-dibromobenzene para-dibromobenzene and mixtures thereof in the presence of a sodium base.Type: GrantFiled: November 28, 1980Date of Patent: October 26, 1982Assignee: Gulf Research & Development CompanyInventors: James J. Harrison, Edward T. Sabourin, Charles M. Selwitz
-
Patent number: 4349568Abstract: Novel compounds exhibiting antiviral activity are disclosed, such compounds are represented by the formula: ##STR1## wherein m represents the integer 0, 1 or 2; R represents trihalomethyl, alkyl or phenyl; R.sub.1 represents hydrogen, bromo, chloro, fluoro, cyano, nitro, amino, alkyl, alkoxy or trifluoromethyl; R.sub.2 represents hydroxyl, bromo, chloro, fluoro, cyano, acetyl, benzoyl, substituted benzoyl, alkyl, alkoxy, substituted alkoxy, benzyl, substituted benzyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, or the radical --O(CH.sub.2).sub.n R.sub.4 wherein n represents the integer 1, 2 or 3 and R.sub.4 represents cyano or dialkylamino; R.sub.3 represents hydrogen, hydroxyl, bromo, chloro, fluoro, cyano, acetyl, benzoyl, substituted benzoyl, alkyl, alkoxy, substituted alkoxy, benzyl, substituted benzyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, or the radical --O(CH.sub.2).sub.n R.sub.Type: GrantFiled: June 12, 1980Date of Patent: September 14, 1982Assignee: The Dow Chemical CompanyInventors: Lowell D. Markley, Yulan C. Tong, Steven G. Wood
-
Patent number: 4338468Abstract: .alpha.-Prop-1-ynyl-3-phenoxybenzyl alcohols of the formula ##STR1## wherein Y represents hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, cyano or dimethylamino, a process for their manufacture and their use as intermediates for the synthesis of compounds which are suitable for pest control, and which are especially suitable because of their low fish toxicity, for the control of rice pests e.g. Chilo suppressalis in rice paddies where fish are kept.Type: GrantFiled: December 9, 1980Date of Patent: July 6, 1982Assignee: Ciba-Geigy CorporationInventors: Saleem Farooq, Peter Ackermann, Jozef Drabek, Laurenz Gsell, Odd Kristiansen, Rudolf Wehrli
-
Patent number: 4331817Abstract: A process for the preparation of a 4-arylthioaniline from the corresponding 4-unsubstituted aniline which comprises reacting the latter with an alkali metal thiocyanate in the presence of halogen to provide the 4-thiocyanoaniline, reacting it with an alkali metal sulfide to convert the thiocyano moiety to an alkali metal mercaptide group followed by heating with cuprous oxide then with an aryl halide to form the desired product.Type: GrantFiled: January 16, 1981Date of Patent: May 25, 1982Assignee: Minnesota Mining and Manufacturing Co.Inventor: James R. Throckmorton
-
Patent number: 4314078Abstract: Preparation of a compound of the following formula (I): ##STR1## wherein R.sup.1 is alkyl of 1 to 12 carbons, from the compound of the following formula (II): ##STR2## by the steps of coupling (II) with 3,4-dichlorobenzotrifluoride; reacting the --NH.sub.2 and COOH groups with a COX.sub.2 compound, X being a leaving group, to produce a heterocycle; opening the heterocycle with an alkanesulphonamide; and oxidizing the resultant --NH.sub.2 group to an --NO.sub.2 to yield a compound of formula (I). Novel intermediates are also described. Compounds of formula (I) are useful as selective pre- and post-emergent herbicides.Type: GrantFiled: April 2, 1981Date of Patent: February 2, 1982Assignee: ICI Americas Inc.Inventors: Walter M. Kruse, John F. Stephen
-
Patent number: 4314086Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Daniel Michelet
-
Patent number: 4313000Abstract: The invention comprises the preparation of a compound of the following formula (I): ##STR1## wherein R.sup.1 is alkyl of 1 to 12 carbons, from the compound of the following formula (II): ##STR2## by the steps of coupling (II) with 3,4-dichlorobenzotrifluoride; reacting the --NH.sub.2 group with an XCOOR compound, X being a leaving group with R an organic moiety; oxidizing the --CH.sub.3 group to a --COOH group; cyclization to produce a heterocycle with loss --OR; opening the heterocycle with an alkanesulphonamide; and oxidizing the resultant --NH.sub.2 group to an NO.sub.2 to yield a compound of formula (I). Novel intermediates are also described. Compounds of formula (I) are useful as selective pre- and post-emergent herbicides.Type: GrantFiled: April 2, 1981Date of Patent: January 26, 1982Assignee: ICI Americas Inc.Inventors: Walter M. Kruse, John F. Stephen
-
Patent number: 4310693Abstract: o-Aminophenol derivatives are described represented by the formula (I) ##STR1## wherein R represents --NH.sub.2 or --NH--CO--R.sup.6 ; R.sup.1 and R.sup.2 which may be the same or different, each can represent an alkyl group or an aromatic group, or R.sup.1 and R.sup.2 together can form a ring; or R.sup.1, R.sup.2 and R.sup.3 together can form a ring ; R.sup.3 represents hydrogen, an alkyl group or an aromatic group; R.sup.4 can represent an alkyl group or an aromatic group; R.sup.5 can represent an alkyl group, an alkoxy group, an alkylthio group, an arylthio group, a halogen atom or an acylamino group; and n is 0, 1 or 2; R.sup.6 represents an alkyl group or an aromatic group; and R.sup.4 and R.sup.5 together can form a heterocyclic ring, R.sup.1 and R.sup.4 together can form a heterocyclic ring, or R.sup.1 and R.sup.5 together can form a ring; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5.sub.n have a total of 7 or more carbon atoms.Type: GrantFiled: July 18, 1980Date of Patent: January 12, 1982Assignee: Fuji Photo Film Co., Ltd.Inventors: Shinsaku Fujita, Koichi Koyama, Yoshio Inagaki
-
Patent number: 4288386Abstract: The Ullman reaction for the preparation of diaryl ethers by coupling aryl halides with metal phenolates is conducted in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: May 12, 1980Date of Patent: September 8, 1981Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Louis Linguenheld
-
Patent number: 4287125Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: September 1, 1981Assignee: Rhone-Poulenc IndustriesInventor: Gerard Soula
-
Patent number: 4279637Abstract: This invention discloses chemical compounds of the formula ##STR1## wherein X and Z are each independently selected from the group consisting of halogen, haloalkyl, nitro, cyano, alkyl, alkoxy and alkylthio; m and n are each independently integers of from 0 to 4; Y is selected from the group consisting of oxygen, sulfur, methylene, sulfonyl and sulfinyl; and R is selected from the group consisting of hydrogen, alkyl and alkoxy. The compounds of the above description are useful as herbicides.Type: GrantFiled: May 29, 1980Date of Patent: July 21, 1981Assignee: Velsicol Chemical CorporationInventor: Frank Wu
-
Patent number: 4277624Abstract: Novel diphenyl ether compounds of the general formula: ##STR1## wherein X represents a hydrogen atom or a nitro group, process for preparing the same and diphenyl ethers of the general formula: ##STR2## wherein R represents a hydrogen atom, or substituted or unsubstituted alkyl group, alkenyl group or alkynyl group, and Y represents an oxygen atom, a sulfur atom, or the group ##STR3## wherein R' is defined as R above, by reacting 2-chloro-4-trifluoromethylphenyl-3,4-dinitrophenyl ether with a compound of the general formula:RYH (III)wherein R and Y have the same meanings as defined above, respectively. The latter diphenyl ether compounds of the general formula (II) are useful as herbicides.Type: GrantFiled: July 5, 1979Date of Patent: July 7, 1981Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Takeo Yoshimoto, Keiichi Igarashi, Kengo Oda, Masaaki Ura, Naoki Sato
-
Patent number: 4239880Abstract: New polynuclear aromatic diamines, such as 2,2'-di-(p-aminophenoxy)-biphenyl, a process for their manufacture and their use as polycondensation components for the manufacture of polyamide, polyamide-imide and polyimide polymers are described. The polymers obtained with the aromatic diamines according to the invention are readily soluble and can also be processed from the melt and are distinguished by good thermal, electrical and/or mechanical properties.Type: GrantFiled: July 17, 1979Date of Patent: December 16, 1980Assignee: Ciba-Geigy CorporationInventor: Roland Darms
-
Patent number: 4231757Abstract: Nitrogen-containing compositions made by condensing a nitro phenol with an organic amino compound having at least one hydrogen atom directly bonded to a nitrogen or oxygen atom are useful as additives for lubricants and fuels. A specific embodiment comprises compositions made by reacting nitro phenols having hydrocarbyl substituents of up to 750 aliphatic carbon atoms with alkylene polyamines.Type: GrantFiled: June 2, 1978Date of Patent: November 4, 1980Assignee: The Lubrizol CorporationInventor: Kirk E. Davis