Two Benzene Rings Bonded Directly To The Same Oxygen, Sulfur, Or Polysulfide Chain Patents (Class 564/430)
  • Patent number: 4694105
    Abstract: 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: Grant
    Filed: December 10, 1984
    Date of Patent: September 15, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Dieter Durr
  • Patent number: 4692554
    Abstract: 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: Grant
    Filed: August 7, 1984
    Date of Patent: September 8, 1987
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Keizaburo Yamaguchi, Yukihiro Yoshikawa, Yoshimitsu Tanabe, Kenichi Sugimoto, Akihiro Yamaguchi
  • Patent number: 4683333
    Abstract: 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: Grant
    Filed: November 22, 1985
    Date of Patent: July 28, 1987
    Assignee: The Dow Chemical Company
    Inventors: Thomas R. Britt, Willie C. Burton
  • Patent number: 4670597
    Abstract: (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: Grant
    Filed: November 8, 1985
    Date of Patent: June 2, 1987
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Robert L. Davis
  • Patent number: 4670598
    Abstract: (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: Grant
    Filed: November 8, 1985
    Date of Patent: June 2, 1987
    Assignee: Ethyl Corporation
    Inventor: Robert L. Davis
  • Patent number: 4665000
    Abstract: 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: Grant
    Filed: October 19, 1984
    Date of Patent: May 12, 1987
    Assignee: Xerox Corporation
    Inventors: Emery G. Tokoli, Anthony M. Horgan
  • Patent number: 4663483
    Abstract: 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: Grant
    Filed: May 15, 1985
    Date of Patent: May 5, 1987
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Robert G. Bass, Mark S. Sinsky, John W. Connell
  • Patent number: 4663484
    Abstract: 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: Grant
    Filed: November 25, 1985
    Date of Patent: May 5, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventor: Walter Horstmann
  • Patent number: 4662935
    Abstract: 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: Grant
    Filed: September 16, 1981
    Date of Patent: May 5, 1987
    Assignee: Rohm and Haas Company
    Inventors: Horst O. Bayer, Colin Swithenbank, Roy Y. Yih
  • Patent number: 4650905
    Abstract: 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: Grant
    Filed: September 11, 1985
    Date of Patent: March 17, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Adolf Parg, Gerhard Hamprecht, Bruno Wuerzer
  • Patent number: 4633016
    Abstract: 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: Grant
    Filed: August 6, 1985
    Date of Patent: December 30, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Josef Witt, Zsolt Szentivanyi
  • Patent number: 4613619
    Abstract: 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: Grant
    Filed: February 22, 1985
    Date of Patent: September 23, 1986
    Assignee: AKZO N.V.
    Inventors: Thomas Sleigh, David S. Savage, John K. Clark
  • Patent number: 4603222
    Abstract: 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: Grant
    Filed: August 30, 1984
    Date of Patent: July 29, 1986
    Assignee: Occidental Chemical Corporation
    Inventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
  • Patent number: 4594453
    Abstract: (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: Grant
    Filed: June 11, 1984
    Date of Patent: June 10, 1986
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Bonnie G. McKinnie
  • Patent number: 4576857
    Abstract: 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: Grant
    Filed: September 21, 1983
    Date of Patent: March 18, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Thomas P. Gannett, Hugh H. Gibbs
  • Patent number: 4566900
    Abstract: 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: Grant
    Filed: December 1, 1982
    Date of Patent: January 28, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Plath, Ulrich Schirmer, Gernot Reissenweber, Bruno Wuerzer, Guenter Retzlaff
  • Patent number: 4566876
    Abstract: 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: Grant
    Filed: March 10, 1983
    Date of Patent: January 28, 1986
    Assignee: Clairol Incorporated
    Inventors: Keith C. Brown, John F. Corbett
  • Patent number: 4551551
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: November 5, 1985
    Assignee: Mallinckrodt, Inc.
    Inventor: Ervin B. Inskip
  • Patent number: 4548976
    Abstract: 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: Grant
    Filed: May 18, 1984
    Date of Patent: October 22, 1985
    Assignee: The Dow Chemical Company
    Inventors: Pierre DeRoche, Neil V. Kirby
  • Patent number: 4539428
    Abstract: 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: Grant
    Filed: May 10, 1982
    Date of Patent: September 3, 1985
    Assignee: Mallinckrodt, Inc.
    Inventors: Philip H. Merrell, Michael F. Ellis
  • Patent number: 4526608
    Abstract: Substituted phenoxyphenylhydroxyamines and pyridyloxyphenylhydroxyamines, and the use thereof for the control of weeds.
    Type: Grant
    Filed: March 31, 1983
    Date of Patent: July 2, 1985
    Assignee: Zoecon Corporation
    Inventor: Shy-Fuh Lee
  • Patent number: 4521623
    Abstract: 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: Grant
    Filed: February 17, 1984
    Date of Patent: June 4, 1985
    Assignee: TRW Inc.
    Inventors: Robert J. Jones, Glenn E. C. Chang
  • Patent number: 4514574
    Abstract: Separate isomers via supercritical gas extraction.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: April 30, 1985
    Assignee: The Dow Chemical Company
    Inventors: Kimio Inoue, Gale G. Hoyer, Stanley I. Bates
  • Patent number: 4506100
    Abstract: 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: Grant
    Filed: August 4, 1982
    Date of Patent: March 19, 1985
    Assignee: National Starch and Chemical Corporation
    Inventors: Jules E. Schoenberg, Stephen P. Anderson
  • Patent number: 4469893
    Abstract: 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: Grant
    Filed: March 22, 1982
    Date of Patent: September 4, 1984
    Assignee: Occidental Chemical Corporation
    Inventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
  • Patent number: 4454350
    Abstract: 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: Grant
    Filed: June 28, 1982
    Date of Patent: June 12, 1984
    Assignee: Rhone-Poulenc Specialities Chimiques
    Inventor: Michel Desbois
  • Patent number: 4401461
    Abstract: 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: Grant
    Filed: March 16, 1978
    Date of Patent: August 30, 1983
    Assignee: Rohm and Haas Company
    Inventors: Harold F. Wilson, Marvin H. Fleischfresser
  • Patent number: 4393079
    Abstract: 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: Grant
    Filed: December 15, 1976
    Date of Patent: July 12, 1983
    Assignee: Beecham Group Limited
    Inventors: William G. Cole, Alexander C. Goudie, Carl J. Rose
  • Patent number: 4378298
    Abstract: 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: Grant
    Filed: May 12, 1981
    Date of Patent: March 29, 1983
    Assignee: UOP Inc.
    Inventor: John T. Roberts
  • Patent number: 4377532
    Abstract: 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: Grant
    Filed: February 19, 1982
    Date of Patent: March 22, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
  • Patent number: 4375562
    Abstract: 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: Grant
    Filed: February 26, 1981
    Date of Patent: March 1, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Theodor Pfister, Rolf Putter
  • Patent number: 4370501
    Abstract: 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: Grant
    Filed: October 5, 1981
    Date of Patent: January 25, 1983
    Assignee: Hughes Aircraft Company
    Inventor: Kreisler S. Y. Lau
  • Patent number: 4364875
    Abstract: 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: Grant
    Filed: July 7, 1981
    Date of Patent: December 21, 1982
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Richard Sehring, Wolfgang Buck
  • Patent number: 4360375
    Abstract: 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: Grant
    Filed: December 23, 1980
    Date of Patent: November 23, 1982
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
  • Patent number: 4358308
    Abstract: The 4-perfluoroacetyl-, 4-perfluoromethylthio-, 4-perfluoromethylsulfinyl-, and 4-perfluoromethylsulfonyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: November 9, 1982
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4356325
    Abstract: 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: Grant
    Filed: November 28, 1980
    Date of Patent: October 26, 1982
    Assignee: Gulf Research & Development Company
    Inventors: James J. Harrison, Edward T. Sabourin, Charles M. Selwitz
  • Patent number: 4349568
    Abstract: 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: Grant
    Filed: June 12, 1980
    Date of Patent: September 14, 1982
    Assignee: The Dow Chemical Company
    Inventors: Lowell D. Markley, Yulan C. Tong, Steven G. Wood
  • Patent number: 4338468
    Abstract: .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: Grant
    Filed: December 9, 1980
    Date of Patent: July 6, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Saleem Farooq, Peter Ackermann, Jozef Drabek, Laurenz Gsell, Odd Kristiansen, Rudolf Wehrli
  • Patent number: 4331817
    Abstract: 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: Grant
    Filed: January 16, 1981
    Date of Patent: May 25, 1982
    Assignee: Minnesota Mining and Manufacturing Co.
    Inventor: James R. Throckmorton
  • Patent number: 4314086
    Abstract: 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: Grant
    Filed: June 20, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Daniel Michelet
  • Patent number: 4314078
    Abstract: 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: Grant
    Filed: April 2, 1981
    Date of Patent: February 2, 1982
    Assignee: ICI Americas Inc.
    Inventors: Walter M. Kruse, John F. Stephen
  • Patent number: 4313000
    Abstract: 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: Grant
    Filed: April 2, 1981
    Date of Patent: January 26, 1982
    Assignee: ICI Americas Inc.
    Inventors: Walter M. Kruse, John F. Stephen
  • Patent number: 4310693
    Abstract: 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: Grant
    Filed: July 18, 1980
    Date of Patent: January 12, 1982
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinsaku Fujita, Koichi Koyama, Yoshio Inagaki
  • Patent number: 4288386
    Abstract: 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: Grant
    Filed: May 12, 1980
    Date of Patent: September 8, 1981
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Louis Linguenheld
  • Patent number: 4287125
    Abstract: 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: Grant
    Filed: June 20, 1980
    Date of Patent: September 1, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • Patent number: 4279637
    Abstract: 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: Grant
    Filed: May 29, 1980
    Date of Patent: July 21, 1981
    Assignee: Velsicol Chemical Corporation
    Inventor: Frank Wu
  • Patent number: 4277624
    Abstract: 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: Grant
    Filed: July 5, 1979
    Date of Patent: July 7, 1981
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Takeo Yoshimoto, Keiichi Igarashi, Kengo Oda, Masaaki Ura, Naoki Sato
  • Patent number: 4239880
    Abstract: 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: Grant
    Filed: July 17, 1979
    Date of Patent: December 16, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Roland Darms
  • Patent number: 4231757
    Abstract: 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: Grant
    Filed: June 2, 1978
    Date of Patent: November 4, 1980
    Assignee: The Lubrizol Corporation
    Inventor: Kirk E. Davis