Halogen Containing Patents (Class 568/637)
  • Patent number: 10745334
    Abstract: The disclosure discloses a method for synthesizing 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl alcohol from 1,4-bis(methoxymethyl)-2,3,5,6-tetrafluorobenzene, belongings to the technical field of organic synthesis. 1,4-bis(methoxymethyl)-2,3,5,6-tetrafluorobenzene reacts in mixed solution consisting of sulfuric acid aqueous solution and organic carboxylic acid, the obtained mixture is subjected to ester group hydrolysis reaction in the presence of an inorganic base and then to hydroxyl methylation reaction, 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl alcohol is finally obtained via separation and purification, and 1,4-bis(methoxymethyl)-2,3,5,6-tetrafluorobenzene is recovered. The disclosure not only realizes the resource utilization of low-value 1,4-bis(methoxymethyl)-2,3,5,6-tetrafluorobenzene, and meanwhile has the advantages of mild reaction conditions, simple operation, high synthesis yield, good product quality and the like. The disclosure has high social and economic values.
    Type: Grant
    Filed: March 8, 2020
    Date of Patent: August 18, 2020
    Inventors: Qiliang Yuan, Jingde Zhang, Haifeng Chen, Yixin Cui, Yinhao Chen, Chao Wang
  • Patent number: 10548825
    Abstract: The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto.
    Type: Grant
    Filed: August 4, 2015
    Date of Patent: February 4, 2020
    Assignee: Unigen, Inc.
    Inventors: Qi Jia, Ji-Fu Zhao
  • Publication number: 20140243194
    Abstract: The present invention relates to substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkynyloxy-ethyl}-1H-[1,2,4]triazole compounds of formula I as defined in the description, and the N-oxides, and salts thereof, processes and intermediates for preparing these compounds and also to compositions comprising at least one such compound. The invention also relates to the use of such compounds and compositions for combating harmful fungi and seed coated with at least one such compound.
    Type: Application
    Filed: August 14, 2012
    Publication date: August 28, 2014
    Applicant: BASF SE
    Inventors: Jochen Dietz, Richard Riggs, Nadege Boudet, Jan Klaas Lohmann, Ian Robert Craig, Egon Haden, Erica May Wilson Lauterwasser, Bernd Mueller, Wassilios Grammenos, Thomas Grote
  • Publication number: 20140162876
    Abstract: The present invention relates to substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)phenyl]-2-ethoxy-ethyl}-1H-[1,2,4]triazole compounds of formula I as defined in the description, and the N-oxides, and salts thereof, processes and intermediates for preparing these compounds and also to compositions comprising at least one such compound. The invention also relates to the use of such compounds and compositions for combating harmful fungi and seed coated with at least one such compound.
    Type: Application
    Filed: August 14, 2012
    Publication date: June 12, 2014
    Applicant: BASF SE
    Inventors: Jochen Dietz, Richard Riggs, Nadege Boudet, Jan Klaas Lohmann, Ian Robert Craig, Egon Haden, Erica May Wilson Lauterwasser, Bernd Mueller, Wassilios Grammenos, Thomas Grote
  • Publication number: 20140141973
    Abstract: The present invention relates to alkyl- and aryl-substituted 2-[2-chloro-4-(dihalo-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds of formula I as defined in the description, and the N-oxides, and salts thereof, processes and intermediates for preparing these compounds and also to compositions comprising at least one such compound. The invention also relates to the use of such compounds and compositions for combating harmful fungi and seed coated with at least one such compound.
    Type: Application
    Filed: July 12, 2012
    Publication date: May 22, 2014
    Applicant: BASF SE
    Inventors: Jochen Dietz, Richard Riggs, Nadege Boudet, Jan Klaas Lohmann, Ian Robert Craig, Egon Haden, Erica May Wilson Lauterwasser, Bernd Mueller, Wassilios Grammenos, Thomas Grote
  • Publication number: 20140105839
    Abstract: The present invention relates to a compound of the following formula (I): as well as its process of preparation, pharmaceutical and cosmetics composition comprising it and use thereof, notably as an inhibitor of the sodium-dependent glucose co-transporter, such as SGLT1, SGLT2 and SGLT3, in particular in the treatment or prevention of diabetes, and more particularly type-II diabetes, diabetes-related complications, such as arthritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy or blindness, hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, X syndrome and arteriosclerosis, as well as for its use as an anticancer, anti-infective, anti-viral, anti-thrombotic or anti-inflammatory drug, or for lightening, bleaching, depigmenting the skin, removing blemishes from the skin, particularly age spots and freckles, or preventing pigmentation of the skin.
    Type: Application
    Filed: May 29, 2012
    Publication date: April 17, 2014
    Applicant: TF-CHEM
    Inventors: Geraldine Deliencourt-Godefroy, Lenaig Lopes
  • Publication number: 20130331413
    Abstract: Disclosed are compositions and methods for treating and/or preventing infections in mammals, by administering to a mammal a therapeutically effective amount of at least one defensin-like molecule, e.g., in a composition that includes such molecule. Also disclosed are kits that include such molecules, or compositions that include such molecules, as well as instructions for using such molecules to treat a mammal.
    Type: Application
    Filed: June 6, 2013
    Publication date: December 12, 2013
    Inventors: Erik DE LEEUW, Alexander D. MACKERELL, JR.
  • Publication number: 20130109758
    Abstract: This invention provides compounds having a structure of Formula (I). Uses of such compounds for treatment of various indications, including prostate cancer as well as methods of treatment involving such compounds are also provided.
    Type: Application
    Filed: January 6, 2011
    Publication date: May 2, 2013
    Applicants: THE UNIVERSITY OF BRITISH COLUMBIA, BRITISH COLUMBIA CANCER AGENCY BRANCH
    Inventors: Marianne D. Sadar, Nasrin R. Mawji, Carmen Adriana Banuelos, Raymond J. Andersen, Javier Garcia Fernandez
  • Publication number: 20130018026
    Abstract: The present invention provides compositions and methods for the targeted delivery, release and/or formation of a drug compound at a target site(s) within the body of an individual, such as a diseased and/or inflamed tissue in the body of the individual. These compositions may comprise a halogenated phenol ring cleavably linked to a core structure of a drug compound. Due to the variety of substituents that may be utilized in forming the different types of linkages, numerous examples of drug compounds linked to a halogenated phenol ring are proposed. The present invention further provides compositions comprising halogenated phenol starting compounds that do not undergo cleavage during a dehalogenation reaction to form a drug compound in a targeted tissue when administered to an individual. Methods of administering these non-cleaving compounds are further provided.
    Type: Application
    Filed: July 13, 2012
    Publication date: January 17, 2013
    Inventor: Keith R. Latham
  • Publication number: 20120316227
    Abstract: Embodiments of antimicrobial chrysophaentin compounds, pharmaceutical compositions including the chrysophaentin compounds, and methods for using the chrysophaentin compounds are disclosed. Some embodiments of the disclosed compounds are isolated from Chrysophaeum taylori. Certain embodiments of the chrysophaentin compounds inhibit FtsZ protein, thereby inhibiting the growth of clinically relevant bacteria, including drug-resistant strains.
    Type: Application
    Filed: February 25, 2011
    Publication date: December 13, 2012
    Inventors: Carole A. Bewley, Alberto Plaza, Jessica Keffer
  • Publication number: 20120065297
    Abstract: A halogenated non-polymeric phenyl ether flame retardant is described having the general formula (I): wherein each X is independently Cl or Br, n is an integer of 1 or 2, and each p is independently an integer of 1 to 4, provided that, when each X is Cl, the total amount halogen in the ether is from about 50 to about 65 wt % and when each X is Br, the total amount halogen in the ether is from at least 70 wt % to about 79 wt % and wherein from about 30% to about 80%, for example from about 35% to about 75% of the halogenated ethers are fully halogenated the remainder being partially halogenated. The present flame retardant provides superior mechanical properties when incorporated into a polymer than similar flame retardants which contain a higher amount of fully halogenated species.
    Type: Application
    Filed: September 29, 2011
    Publication date: March 15, 2012
    Applicant: Chemtura Corporation
    Inventors: Larry D. Timberlake, James D. Siebecker, Subramaniam Narayan
  • Publication number: 20110184107
    Abstract: A halogenated non-polymeric phenyl ether is described having the general formula (I): wherein each X is independently Cl or Br, n is an integer of 1 or 2, each m is independently an integer of 1 to 5 and each p is independently an integer of 1 to 4, provided that, when X is Cl, the total amount halogen in the ether is from about 50 to about 65 wt % and when, X is Br, the total amount halogen in the ether is from at least 70 wt % to about 79 wt %.
    Type: Application
    Filed: January 25, 2010
    Publication date: July 28, 2011
    Applicant: CHEMTURA CORPORATION
    Inventor: Larry D. Timberlake
  • Patent number: 7951877
    Abstract: A process, advantageous in producibility, for the production of a vinyl compound containing very small amounts of ionic impurities and hydrolysable halogens, which is capable of curing by means of heat and/or light and giving a cured product having excellent dielectric characteristics and heat resistance, which process can efficiently remove a generated salt and comprises reacting a non-protonic polar solvent solution of a specific bifunctional phenylene ether oligomer with a vinylbenzyl halide in the presence of an alkoxide of an alkali metal, wherein the thus-obtained reaction solution is acidified with a specific amount of an acidic substance, then a salt generated is removed, an alkali substance containing a specific amount of an alkali metal is added to the thus-obtained solution, then a salt generated is removed, and the thus-obtained solution is mixed with water or a water-alcohol mixed solution, to precipitate a solid.
    Type: Grant
    Filed: June 17, 2008
    Date of Patent: May 31, 2011
    Assignee: Mitaubishi Gas Chemical Company, Inc.
    Inventors: Jun Nakano, Takeru Horino, Makoto Miyamoto, Atsushi Hirashima, Yasumasa Norisue
  • Patent number: 7541417
    Abstract: A process comprising the steps of dissolving a dihydric phenol in a solvent to form a solution A, contacting the solution A with an adsorbent material selected from the group consisting of metal oxides, modified metal oxides, activated carbons, and clays, filtering the adsorbent material to form a solution B, adding an anti-solvent to the solution B to form a solution C, and distilling the solution C, wherein the dihydric phenol is represented by Formula (I): wherein R is a hydrogen atom or an aliphatic functionality having 1 to 6 carbon atoms and n is an integer having a value of 1 to 4.
    Type: Grant
    Filed: March 30, 2006
    Date of Patent: June 2, 2009
    Assignee: SABIC Innovative Plastics IP B.V.
    Inventors: Sunil Ashtekar, Mahesh Malusare, Gurram Kishan, Pushpa Narayanan, Ramanarayanan GV, Arun Dixit, Pradeep Nadkarni, Jan Plen Lens
  • Patent number: 7528210
    Abstract: A process comprising the steps of dissolving a dihydric phenol in a solvent to form a solution A; contacting the solution A with a zeolite; filtering the zeolite to form a solution B; adding an anti-solvent to the solution B to form a solution C; and distilling the solution C; wherein the dihydric phenol is represented by Formula (I): wherein R is a hydrogen atom or an aliphatic functionality having 1 to 6 carbon atoms and n is an integer having a value 1 to 4.
    Type: Grant
    Filed: March 30, 2006
    Date of Patent: May 5, 2009
    Assignee: SABIC Innovative Plastics IP B.V.
    Inventors: Guohua Xiu, Tong Sun, Jan Plen Lens, Sunil Ashtekar, Mahesh Malusare, Gurram Kishan, Pushpa Narayanan
  • Patent number: 6706930
    Abstract: There is described a process for the preparation of halogenated hydroxydiphenyl compounds of formula (1) by acylation of a halogenated benzene compound (first stage), etherification of the acylated compound with a halogenated phenol compound, which is not further substituted in the ortho-position (second stage), oxidation of the etherified compound (third stage) and hydrolysis of the oxidized compound in a fourth stage, wherein the reaction of the second stage is carried out in the presence of K2CO3 and any desired copper catalyst, where K2CO3 is used in a concentration of from 0.5 to 30 mol, based on the phenol compound employed of formula (6), according to the reaction scheme (I) in which R1 and R2 independently of one another are F, Cl or Br; R3 and R4 independently of one another are hydrogen; or C1-C4alkyl; m is 1 to 3; and n is 1 or 2. The compounds of formula (1) are used for protecting organic materials and articles from microorganisms.
    Type: Grant
    Filed: October 31, 2002
    Date of Patent: March 16, 2004
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Armando Di Teodoro, Werner Hölzl, Dieter Reinehr, Rudolf Zink
  • Patent number: 6689919
    Abstract: The synthesis of fluoropolyarylene ether with a high degree of polymerization is enabled, by using a copper complex catalyst with an oxidation potential in the range of −1V to 2V, for the oxidative polymerization of fluorophenols that contain at least one hydrogen atom as well as a fluorine atom bonded to the carbon atoms constituting the benzene ring.
    Type: Grant
    Filed: September 7, 2001
    Date of Patent: February 10, 2004
    Assignee: Japan Science and Technology Corporation
    Inventors: Eishun Tsuchida, Kenichi Oyaizu, Yosuke Kumaki, Kei Saito
  • Patent number: 6689920
    Abstract: A process for producing 2,2′,3,3′,5,5′-hexamethyl-[1,1′-biphenyl]-4,4′-diol, which process comprises, while setting a pH of a reaction liquid containing an alkaline aqueous solution, a surfactant, a copper catalyst and 2,3,6-trimethylphenol during a reaction in the range of from 8 to 14 and controlling the variation range of the pH of the reaction liquid within ±1, oxidatively coupling the 2,3,6-trimethylphenol with an oxygen-containing gas, and a process for producing a bifunctional phenylene ether oligomer compound having a controlled average molecular weight, comprising carrying out oxidation polymerization under a proper oxygen concentration.
    Type: Grant
    Filed: October 16, 2002
    Date of Patent: February 10, 2004
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kenji Ishii, Kiyonari Hiramatsu, Makoto Miyamoto, Yasumasa Norisue, Katsuhiko Yanagida
  • Patent number: 6610890
    Abstract: Medicaments for treating diabetic complications contain a compound of formula (A), wherein at least one Y or one Y′ is OH, and the remainder are selected from H, Hal, OH, OMe and NO2; X is O, S, keto or a direct link
    Type: Grant
    Filed: January 7, 2002
    Date of Patent: August 26, 2003
    Assignee: O.N.C.E.-(Organizacion Nacional De Cicgos)
    Inventors: Teresa Garcia de Quesada Fort, JesĂşs A De La Fuente Blanco, Ma JesĂşs Martin Lopez, Isabel Reymundo Cuesta
  • Patent number: 6596907
    Abstract: A description is given of a three-step process for the preparation of 4,4′-dihalogen-o-hydroxydiphenyl compounds of formula (1) which comprises: a) hologenating an alkoxyphenol of formula (6) (=a1), reacting the resulting halogenated phenol compound of formula (5) with p-dihalobenzene of formula (4a) in the presence of copper and/or copper salts to the diphenyl ether compound of formula (2) (=a2) and subsequent ether fission to the diphenyl ether compound of formula (1) (=a3); or b) reacting an alkoxyphenol of formula (6) with the halophenol of formula (4b) to the compound of formula (3) (=b1), then halogenating this compound (=b2) and subsequent ether fission of the resulting compound of formula (2) to the diphenyl ether compound of formula (1) (=b3). The compounds of formula (1) are used for protecting organic materials and objects against microorganisms.
    Type: Grant
    Filed: April 3, 2001
    Date of Patent: July 22, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Armando Di Teodoro, Werner Hölzl, Dieter Reinehr, Rudolf Zink
  • Patent number: 6576800
    Abstract: An oxidation polymer of a substituted phenol, obtained by oxidative polymerization of at least one compound selected from the group consisting of a compound of formula (Ia) and a compound of formula (Ib), in which the oxidation polymer has a number-average polymerization degree of 3 or more: wherein R1 to R4 each represent a hydrogen atom and the like; provided that at least one of R1 to R4 represents a substituted or unsubstituted, saturated hydrocarbon group having 10 or more carbon atoms, and R1 and/or R4 represent a hydrogen atom; wherein R11 represents a substituted or unsubstituted, saturated hydrocarbon group having 15 or more carbon atoms, and R12 is the same as R11, or when R12 is different from R11, R12 represents a substituted or unsubstituted hydrocarbon group and the like.
    Type: Grant
    Filed: July 17, 2001
    Date of Patent: June 10, 2003
    Assignees: National Institute of Advanced Industrial Science and Technology, Japan Chemical Innovation Institute
    Inventors: Hideyuki Higashimura, Shiro Kobayashi
  • Publication number: 20020128522
    Abstract: Disclosed is a four-step process for the preparation of 4,4′-dihalogen-o-hydroxydiphenyl compounds of formula 1
    Type: Application
    Filed: May 2, 2002
    Publication date: September 12, 2002
    Inventors: Armando Di Teodoro, Werner Holzl, Dieter Reinehr, Rudolf Zink
  • Patent number: 6342642
    Abstract: The present invention provides novel 1,4-diaryl-2-fluoro-1-buten-3-ol compounds of the structural formula I a method for the preparation of those formula I compounds, and the use of those formula I compounds in the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds of formula II and 1,4-diaryl-2-fluoro-2-butene compounds of formula III
    Type: Grant
    Filed: August 13, 2001
    Date of Patent: January 29, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Yulin Hu, David Allen Hunt
  • Patent number: 6288011
    Abstract: Pesticidal 1,4-diaryl-2,3-difluoro-2-butene compounds having the structural formula I and compositions and methods comprising those compounds for the control of insect and acarid pests.
    Type: Grant
    Filed: November 11, 1998
    Date of Patent: September 11, 2001
    Assignee: American Cyanamid Co.
    Inventors: Terence James Bentley, Keith Douglas Barnes
  • Publication number: 20010003138
    Abstract: It provides a production method of 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol to allow 2,3,5,6-tetrafluoro-1,4-benzenedimethanol to react with an inorganic base in water, and then add dimethyl sulfate and a water-immiscible organic solvent selected from the group consisting of hydrocarbons and ethers to the reaction mixture, or to allow 2,3,5,6-tetrafluoro-1,4-benzenedimethanol to react with an inorganic base in water and said water-immiscible organic solvent, and then to add dimethyl sulfate to the reaction mixture.
    Type: Application
    Filed: November 30, 2000
    Publication date: June 7, 2001
    Inventors: Taro Hirose, Tatsuya Mori
  • Patent number: 6215029
    Abstract: A process for the preparation of halohydroxydiphenyl compounds useful for protecting organic materials and articles from microorganisms, of the formula by acylation of a halogenated benzene compound (first stage), etherification of the acylated compound with a halogenated phenol compound (second stage), oxidation of the etherified compound (third stage) and hydrolysis of the oxidized compound in a fourth stage, according to the following reaction scheme: in which R1 and R2 independently of one another are F, Cl or Br; R3 and R4 independently of one another are hydrogen; or C1-C4alkyl; m is 1 to 3; and n is 1 or 2.
    Type: Grant
    Filed: June 9, 1999
    Date of Patent: April 10, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Urs Burckhardt, Armando Di Teodoro, Werner Hölzl, Dieter Reinehr, Rudolf Zink, Hanspeter Sauter, Uwe Gronde
  • Patent number: 6133483
    Abstract: A process is disclosed for the synthesis of 2,4,4'-trichloro-2'-methoxydiphenyl ether, and it's precursor 2,4,4'-trichloro-2'-bromodiphenyl ether, a novel compound.
    Type: Grant
    Filed: July 30, 1998
    Date of Patent: October 17, 2000
    Inventor: Thomas F. Cleary
  • Patent number: 5994412
    Abstract: A compound represented by the formula I is disclosed: ##STR1## or a pharmaceutically acceptable salt or hydrate thereof. The compound has inhibitory activity against the oncoprotein Raf.Also included are pharmaceutical compositions, methods of treating cancer, cultures of the producing fungal microorganism and methods of fermentative production of the compound.
    Type: Grant
    Filed: July 2, 1998
    Date of Patent: November 30, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Seok H. Lee, Maria T. Diez, Fernando Pelaez, Marina Mojena Sanchez, M. Dolores Vilella Amils, Hans E. Huber, Denis R. Patrick, Otto D. Hensens, Rosalind G. Jenkins, Leeyuan Huang, Annie Z. Zhao, Deborah L. Zink, Anne Dombrowski, Gerald F. Bills
  • Patent number: 5849958
    Abstract: Pesticidal 1,4-diaryl-2-fluoro-2-butene compounds having the structural formula I ##STR1## and compositions and methods comprising those compounds for the control of insect and acarid pests.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: December 15, 1998
    Assignee: American Cyanamid Company
    Inventors: Keith D. Barnes, Yulin Hu
  • Patent number: 5663453
    Abstract: Compounds of the formula ##STR1## in which: n is 0, 1 or 2, and, if n is 2, the two radicals R.sub.3 are identical or different;R.sub.2 is methyl, fluorine, chlorine or bromine;R.sub.3 is C.sub.1 -C.sub.3 -alkyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, halo-C.sub.1 -C.sub.3 alkoxy, fluorine, chlorine or bromine:R.sub.5 is hydrogen or C.sub.1 -C.sub.9 alkyl andX is methylene, O, S or C(.dbd.O):can be used as intermediates for agrochemical active ingredients.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: September 2, 1997
    Assignee: Ciba-Geiby Corporation
    Inventor: Friedrich Karrer
  • Patent number: 5571501
    Abstract: An aqueous based dentifrice containing the potassium salt of 2,4,4'-trichloro-2'-hydroxy-diphenyl ether (Triclosan).
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: November 5, 1996
    Assignee: Colgate Palmolive Company
    Inventor: Arthur Toy
  • Patent number: 5530015
    Abstract: There is disclosed a dihalopropene compound of the formula I: ##STR1## wherein l is an integer of 1 to 5; m is an integer of 1 to 4; R.sup.1 's and R.sup.2 's are the same or different and are independently halogen or various other groups; D is oxygen; X's are the same or different and are independently chlorine or bromine; Y is oxygen; Z, P and Q are the same or different and are independently nitrogen or CH, provided that P and Q are not simultaneously nitrogen, and when Y is sulfur, Z is CH. Also disclosed is an insecticide/acaricide comprising the dihalopropene compound as an active ingredient. The dihalopropene compound exhibits excellent insecticidal/acaricidal action. Further disclosed is an intermediate compound for use in the production of the dihalopropene compound.
    Type: Grant
    Filed: October 19, 1994
    Date of Patent: June 25, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Masaya Suzuki, Toshio Nagatomi, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 5498803
    Abstract: Poly(arylene ether)s containing pendent ethynyl and substituted ethynyl groups and poly(arylene ether) copolymers containing pendent ethynyl and substituted ethynyl groups are readily prepared from bisphenols containing ethynyl and substituted ethynyl groups. The resulting polymers are cured up to 350.degree. C. to provide crosslinked poly(arylene ether)s with good solvent resistance, high strength and modulus.
    Type: Grant
    Filed: March 7, 1994
    Date of Patent: March 12, 1996
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Brian J. Jensen
  • Patent number: 5382686
    Abstract: Nitrodiphenyl(thio) ethers in which the nitro group is in the ortho- or para-position with respect to the ether oxygen or ether sulphur can be prepared from halonitrobenzones in which the nitro group is in the ortho- or para-position with respect to the halogen and, alkali metal (thio)phenolates in liquid ammonia, the reaction being carried out under pressure and at a temperature from -30.degree. C. to +140.degree. C. and the ammonia being separated off after the reaction is completed.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: January 17, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ferdinand Hagedorn, Helmut Fiege
  • Patent number: 5312975
    Abstract: A process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid comprising the reaction of an organometallic derivative with a suitable substituted benzene in the presence of a transition-metal based catalyst is described.
    Type: Grant
    Filed: December 27, 1991
    Date of Patent: May 17, 1994
    Assignee: Zambon Group S.p.A.
    Inventors: Claudio Giordano, Laura Coppi, Francesco Minisci
  • Patent number: 5302760
    Abstract: Stability enhancing additives of the formula: ##STR1## where R.sub.f is a perfluoroalkyl group having 1 to 15 carbon atoms and n has a value of 1 to 6, for perfluoropolyalkylether fluids. These additives are incorporated into perfluoropolyalkylether fluids in an amount ranging from about 0.01 to 3 weight percent.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: April 12, 1994
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Lois J. Gschwender, Carl E. Snyder, Jr.
  • Patent number: 5288742
    Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different, is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: February 22, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Philip N. Edwards, David Waterson
  • Patent number: 5276205
    Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 carboalkoxy, C.sub.2 -C.sub.5 alkylcarbonyl, nitro or cyano;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 haloalkenoxy, nitro, cyano, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 carboalkoxy;R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy;provided that:R.sub.1, R.sub.2 and R.sub.3 are not all hydrogen; orR.sub.1 and R.sub.2 taken together are C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy or halo-C.sub.1 -C.sub.3 alkylenedioxy;R.sub.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: January 4, 1994
    Assignee: ICI Americas Inc.
    Inventor: Karl J. Fisher
  • Patent number: 5258410
    Abstract: An aromatic compound of the formula ##STR1## , which is useful as an insect pest controlling agent.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: November 2, 1993
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Akira Shuto, Noriyasu Sakamoto, Hirosi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda
  • Patent number: 5252610
    Abstract: An aromatic compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are, the same or different, a hydrogen atom, a halogen atom or a methyl group with the proviso that either one of R.sup.1 or R.sup.2 is a hydrogen atom; R.sup.3 is a hydrogen atom or a methyl group; and R.sup.4 is a halogen atom, a C.sub.1 -C.sub.2 alkyl group or a C.sub.1 -C.sub.2 haloalkyl group, which is useful for control of insect pests.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: October 12, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Akira Shuto, Hiroshi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda
  • Patent number: 5250574
    Abstract: An aromatic compound of the formula: ##STR1## wherein R.sup.1 is, the same or different, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy group or a C.sub.1 -C.sub.3 haloalkoxy group; R.sup.2 is a hydrogen atom or a methyl group; R.sup.3 is, the same or different, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.2 alkoxy group or a C.sub.1 -C.sub.2 haloalkoxy group, or two adjacent R.sup.3 s may be combined together to represent a C.sub.1 -C.sub.2 alkylenedioxy group optionally bearing one or two substituents selected from halogen and methyl; p is an integer of 2 to 5; q is an integer of 0 to 5, which is useful for control of insect pests.
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: October 5, 1993
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Noriyasu Sakamoto, Akira Shuto, Hirosi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda
  • Patent number: 5248834
    Abstract: Pesticidal compounds of formula II: R.sub.A CR.sub.3 .dbd.CR.sub.4 CHDR.sub.Bin which formula:R.sub.A represents a group ArCR.sub.1 R.sub.2 - in which Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl or haloalkyl groups;R.sub.1 and R.sub.2 together with the carbon to which they are attached represent a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by one or more halogen atoms or C.sub.1 -C.sub.6 alkyl groups.R.sub.3 and R.sub.4 which may be identical or differ, represent hydrogen halogen or C.sub.1 -C.sub.6 alkyl groups andR.sub.B represents the residue of an alcohol R.sub.B CHDOH in which D is hydrogen or cyano and of which the [1R, cis] 2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylic ester is significantly insecticidal,the configuration of R.sub.A and CHDR.sub.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: September 28, 1993
    Assignee: British Technology Group Limited
    Inventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay, Ahmet Baydar
  • Patent number: 5242996
    Abstract: A modified epoxy resin or compound of the formula: ##STR1## wherein A is the backbone reside of a glycidyl ether epoxy resin with removal of the glycidyloxy groups; R.sup.1 and R.sup.2 are independently a hydrogen atom or C.sub.1 -C.sub.12 alkyl; R.sup.3 is a glycidyl group; and n is an integer of greater than 1. A method for producing the modified epoxy resin is also disclosed.
    Type: Grant
    Filed: May 22, 1991
    Date of Patent: September 7, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
  • Patent number: 5227533
    Abstract: This invention relates to the alk-1-enyl ether having the formula ##STR1##
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: July 13, 1993
    Assignee: ISP Investments Inc.
    Inventors: Jeffrey S. Plotkin, Kolazi S. Narayanan, Paul D. Taylor
  • Patent number: 5225607
    Abstract: This invention relates to novel fluorinated ethers, useful as insecticides and acaricides, to processes and intermediates for their preparation, to insecticidal and acaricidal compositions thereof and to methods of combating and controlling insect and acarine pests therewith.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: July 6, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr, Alan J. Whittle
  • Patent number: 5210321
    Abstract: A process for producing a mixture of brominated diphenyl oxides with an average bromine number of 7.0 to 7.8 is improved by the utilization of a multi-step, multi-catalyst procedure. The process uses a zirconium catalyst in the first reaction and an iron catalyst in the second reaction to yield a whiter flame retardant product having less tendency to discolor plastic resins.
    Type: Grant
    Filed: September 25, 1991
    Date of Patent: May 11, 1993
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Mark A. Templeton
  • Patent number: 5144083
    Abstract: A process for producing a p-hydroxyneophyl m-phenoxybenzyl ether represented by the general formula (II) ##STR1## (X.sub.1 and X.sub.2 are independently a hydrogen atom or a halogen atom) by subjecting a corresponding p-alkoxyneophyl m-phenoxybenzyl ether represented by the general formula (I) ##STR2## (R represents a lower alkyl group, and X.sub.1 and X.sub.2 have the same definitions as above) to ether cleavage, in which process the ether cleavage reaction is effected in an aprotic polar solvent, using a lower alkoxide of an alkali metal or an alkaline earth metal or using a metal hydroxide in the presence of a lower alcohol.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: September 1, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
  • Patent number: 5117010
    Abstract: The present invention relates to the preparation of di-secondary alcohols comprising the reaction of an alcohol and a diglycidyl ether of a dihydric phenol in the presence of a catalyst of the formula (IV):MX (IV)wherein M is a metal from Groups IB to VIIIB or a metal or metalloid from Groups IIA to VA of the Periodic Chart of Elements or an ammonium ion and X is an anion selected from the group consisting of BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, AlF.sub.4.sup.-, TiF.sub.6.sup.2-, SiF.sub.6.sup.2-, and ZrF.sub.6.sup.2- to produce the di-secondary alcohol, which can then be subjected to glycidylation to produce a glycidyl ether, orthe reaction of an alcohol, glycol or polyol and epichlorohydrin in the presence of the foregoing catalyst, followed by ring closure employing an alkali to produce a mono- or polyglycidyl ether. The monoglycidyl ether can be further reacted with a dihydric phenol to produce a di-secondary alcohol which is then glycidylized to produce a glycidyl ether.
    Type: Grant
    Filed: August 15, 1991
    Date of Patent: May 26, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Chi-Wen F. Cheng
  • Patent number: 5114977
    Abstract: There are disclosed 1-[4-(halophenoxy)phenoxy]-4-pentines of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other chloro or fluoro and one of R.sub.1 and R.sub.2 is also hydrogen, a process for their preparation and intermediates for their preparation, the use of these compounds in pest control, and pesticidal compositions which contains a compound of formula I as active component. The preferred field of use is ovicidal control of pests.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: May 19, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Karrer, Alfred Rindlisbacher
  • Patent number: 5105021
    Abstract: A higher yield of the difluorohalomethoxybenzene produced by the reaction of a metal phenolate with dibromodifluoromethane or bromochlorodifluoromethane can be obtained by conducting the addition of a metal alcoholate or a metal hydride as a reaction initiator to a solution or a suspension of an aprotic polar solvent containing the metal phenolate and dibromodifluoromethane or bromochlorodifluoromethane.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: April 14, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto