Polyphenols Patents (Class 568/717)
  • Publication number: 20040267057
    Abstract: Provided is a method for producing a phenol condensate by oxidative condensation of a phenol compound not having a substituted group on at least one ortho-position, in the presence of a specific complex (II) and oxygen, wherein a condensate coupled at para-position of the phenol can be produced in an excellent yield,
    Type: Application
    Filed: May 27, 2004
    Publication date: December 30, 2004
    Inventors: Hideyuki Higashimura, Eiichi Kotake, Masaaki Kubota, Shiro Kobayashi
  • Patent number: 6784228
    Abstract: The present invention relates to an epoxy resin composition a cure article thereof, a novel epoxy resin used therein, a polyhydric phenol compound suited for used as an intermediate thereof, and a process for preparing the same. One of the objects to be achieved by the present invention is to exert the heat resistance, the moisture resistance, the dielectric performances and the flame-resistant effect required of electric or electronic materials such as semiconductor encapsulating materials and varnishes for circuit boards in the epoxy resin composition.
    Type: Grant
    Filed: July 9, 2002
    Date of Patent: August 31, 2004
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Ichiro Ogura, Yoshiyuki Takahashi, Tomoyuki Imada
  • Publication number: 20040167364
    Abstract: There is provided a method for producing a coupling compound of formula (1):
    Type: Application
    Filed: February 18, 2004
    Publication date: August 26, 2004
    Applicant: Sumitomo Chemical Company, Limited
    Inventors: Tamon Itahashi, Takashi Kamikawa
  • Publication number: 20040158074
    Abstract: A class of substituted biphenyl compounds is described for use in treating inflammation and inflammation-related disorders.
    Type: Application
    Filed: January 13, 2004
    Publication date: August 12, 2004
    Applicant: G.D. Searle & Co.
    Inventors: David B. Reitz, James J. Li, Monica B. Norton
  • Publication number: 20040147790
    Abstract: A method for producing 4,4′-biphenol, comprising the steps of:
    Type: Application
    Filed: October 14, 2003
    Publication date: July 29, 2004
    Inventors: Mikio Kawahara, Toyokazu Kitaura
  • Publication number: 20040006235
    Abstract: In a process for the preparation of ring compounds via a combinatorial synthesis, the reaction procedure is based on a Suzuki coupling, subsequent halo-demetallation and finally a further Suzuki coupling. The Suzuki couplings are each carried out with a boronic acid or a boronic acid ester. The reaction procedure uses provides novel ring compounds and uses novel synthesis units used for this purpose. The novel ring compounds are suitable for use as constituents in liquid-crystalline mixtures.
    Type: Application
    Filed: March 17, 2003
    Publication date: January 8, 2004
    Applicant: Merck Patent GmbH
    Inventors: Detlef Pauluth, Peer Kirsch, Peter Baeuerle, Oliver Deeg
  • Publication number: 20030191349
    Abstract: There is described the preparation of phenylphenol compounds of formula (I) by reaction of a keto compound of formula (3) with dioxolane of formula (4) and with an ammonium compound of formula (5) to form a &bgr;-aminoketone compound of formula (6) (reaction step (I)), reaction of the compound of formula (6) with a compound of formula (7) to form a compound of formula (2) (reaction step (II)), and subsequent alkylation to form a compound of formula (I) (reaction step (III)) in accordance with scheme (A); wherein R1, R2, R3, R6 and R7 are each independently of the others hydrogen or C1-C8-alkyl; R4, R5 and R8 are each independently of the others hydrogen or C1-C5alkyl; and Hal is a halogen atom. The compounds prepared in accordance with the invention are suitable as antimicrobial active substances.
    Type: Application
    Filed: February 25, 2003
    Publication date: October 9, 2003
    Inventors: Klaus Nussbaum, Martina Hoffmann
  • Publication number: 20030181748
    Abstract: The invention relates to a method for carrying out CC-coupling reactions, in particular a Heck and Suzuki reaction, in the presence of supported palladium as the catalyst and a base in a monophase or multiphase solvent mixture. According to said method, palladium detaches itself from the support in a characteristic manner, is redeposited after the reaction and the quantity of palladium not deposited after the reaction is significantly lower than 5000 ppm, in relation to the palladium used.
    Type: Application
    Filed: March 6, 2003
    Publication date: September 25, 2003
    Inventors: J?uuml;rgen Krauter, J?ouml;rg Pietsch, Peter Panster, Klaus Khler, Roland Heidenreich
  • Patent number: 6620978
    Abstract: The present invention provides a positive photoresist composition including (A) an alkali-soluble resin and (B) a photosensitizer, and the ingredient (B) is a quinonediazide ester of, for example, 2,6-bis[4-hydroxy-3-(2-hydroxy-3,5-dimethylbenzyl)-2,5-dimethylbenzyl]-4-methylphenol, where the average degree of esterification of 20% to 80%.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: September 16, 2003
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Satoshi Shimatani, Ken Miyagi, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20030171593
    Abstract: The present invention concerns a process for arylating or vinylating or alkynating a nucleophilic compound. More particularly, the invention concerns arylating nitrogent-containing organic derivatives. The arylating or vinylating or alkynating process of the invention consists of reacting a nucleophilic compound with a compound carrying a leaving group and is characterized in that the reaction is carried out in the presence of an effective quantity of a catalyst based on a metallic element M selected from groups (VIII), (Ib) and (IIb) of the periodic table and at least one at least bidentate ligand comprising at least two chelating atoms, namely at least one oxygen atom and at least one nitrogen atom.
    Type: Application
    Filed: May 31, 2002
    Publication date: September 11, 2003
    Inventors: Pascal Philippe Cellier, Henri-Jean Cristau, Jean-Francis Spindler, Marc Taillefer
  • Publication number: 20030158451
    Abstract: The specification provides a method for producing p-cumylphenol phenol by reacting phenol with &agr;-methylstyrene in the presence of a highly efficient heterogeneous aluminum zirconium catalyst.
    Type: Application
    Filed: February 3, 2003
    Publication date: August 21, 2003
    Inventors: Arkady Samuilovich Dyckman, John William Fulmer, Boris V. Krasy, Viktor Vladimirovich Pinson, Yury Alekseevich Shavandin, Genrikh Petrovich Yavshits, Andrey Vladimirovich Zinenkov
  • Patent number: 6600004
    Abstract: A method of preparing polyestercarbonates is presented in which a mixture of at least one activated diaryl carbonate is reacted under melt polymerization conditions with at least one aromatic dihydroxy compound together with at least one dicarboxylic acid. Polyestercarbonates possessing up to about percent 10 mole dicarboxylic acid residues based on the total amount of structural units derived from aromatic dihydroxy compounds are obtained. The method provides both for high levels of incorporation of the dicarboxylic acid into the polyestercarbonate backbone and a high level of polymer endcapping.
    Type: Grant
    Filed: April 10, 2002
    Date of Patent: July 29, 2003
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Paul Michael Smigelski
  • Publication number: 20030139479
    Abstract: A antimicrobial compound, compositions containing the same, and method of using the same for reducing the presence of microorganism on a substrate or in a fluid environment comprising an antimicrobial effective carrier and at least one antimicrobial compounds including non-halogenated biphenyl triol compounds.
    Type: Application
    Filed: December 13, 2002
    Publication date: July 24, 2003
    Inventors: D. Scott Harper, Robert A. Coburn, Andre Soshinsky, Marianne D. Huntley
  • Publication number: 20030100802
    Abstract: A process for making a compound of the formula 1
    Type: Application
    Filed: October 29, 2002
    Publication date: May 29, 2003
    Inventor: Rafael Shapiro
  • Publication number: 20030028055
    Abstract: The present invention is a high-quality bisphenol A wherein the content of sodium is not more than 80 ppb and the content of each element of the group A consisting of iron, nickel, chromium, manganese, lead, and molybdenum is not more than 50 ppb, or a high-quality bisphenol A containing an organic compound such as 9,9′-dimethylxanthene, 2-(4-hydroxyphenyl)-2,4,4-trimethylchroman, 2,2,4-trimethyl-chromene, etc., in an amount of lower than a specific amount, and a preparation process of these high-quality bisphenol A. When an aromatic polycarbonate is prepared using the high-quality bisphenol of the invention, an aromatic polycarbonate which is not colored at the preparation thereof and molding the polycarbonate.
    Type: Application
    Filed: August 2, 2001
    Publication date: February 6, 2003
    Inventors: Hideaki Nakamura, Masamitsu Inomata, Toshizumi Miura
  • Publication number: 20020142923
    Abstract: Hindered tert-butylphenolic antioxidant compositions characterized by a low level of volatile and undesirable single-ring tert-butylphenolic antioxidants and a high level of non-volatile multi-ring (or methylene bridged) tert-butylphenolic antioxidants are obtained by reacting a specific mixture of ultra pure ortho-tert-butylphenol (OTBP), ultra pure 2,6-di-tert-butylphenol (DTBP) and formaldehyde in a solvent in the presence of catalyst. These antioxidants are further characterized by having a low level of 2,6-di-tert-butylphenol, low levels of ortho-tert-butylphenol, and trace levels of 2,4,6-tri-tert-butylphenol.
    Type: Application
    Filed: March 8, 2002
    Publication date: October 3, 2002
    Inventor: Vincent J. Gatto
  • Patent number: 6414106
    Abstract: The present invention relates to a method of neutralizing residual acid species in crude dihydric phenol comprising the step of introducing a thermally stable organic base selected from the group consisting of tetraalkyl phosphonium hydroxides, tetraorganophosphonium carboxylic acid salts, or a mixture thereof into the crude dihydric phenol.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: July 2, 2002
    Assignee: General Electric Company
    Inventors: Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Patrick Joseph McCloskey
  • Patent number: 6399740
    Abstract: Phenol aralkyistion polymers can be prepared by reaction among a phenolic monomer, at least one styrenic monomer and an aryl diolefin. A phenolic monomer can be initially aralkylated in the presence of an acid catalyst with a first portion of at least one styrenic monomer to obtain an aralkylated phenol. The aralkylated phenol thereafter can be reacted with an aryl diolefin to obtain a phenol aralkylation polymer. Optionally, (though preferably) the phenol aralkylation polymer is further aralkylated with a second portion of at least one styrenic monomer. By employing specific catalyst concentrations, reactant concentrations, reaction temperatures, and reaction times, the formation of mono-functional and non-functional by-products is substantially reduced.
    Type: Grant
    Filed: July 6, 1999
    Date of Patent: June 4, 2002
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Edward Lucas, Jr., David A. Hutchings, Rajan Hariharan, Syed A. Elahi, David J. Bir
  • Patent number: 6384288
    Abstract: A process for producing bis(4-hydroxyaryl)alkane is disclosed. The process comprise in sequence the steps of (a) passing inert gas through a melt at 150 to 230° C. that contains bis(4-hydroxyaryl)alkane and other aromatic hydroxy compounds, under conditions designed to remove said other aromatic hydroxy compounds from said melt and to obtain a stream of inert gas that contains said other aromatic hydroxy compounds (b) condensing the stream obtained in (a) to remove said other aromatic hydroxy compound, and to obtain a stream of inert gas, and (c) purifying and compressing the stream of inert gas obtained in (b), and recycling to step (a).
    Type: Grant
    Filed: April 16, 2001
    Date of Patent: May 7, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Steffen Kühling, Rolf Lanze, Rainer Neumann, Frieder Heydenreich, Tony van Osselaer
  • Publication number: 20010020116
    Abstract: There is disclosed an improved process for the preparation of a compound of the formula I 1
    Type: Application
    Filed: January 5, 2001
    Publication date: September 6, 2001
    Inventors: Fabio Pizzoli, Reto Luisoli, Gerrit Knobloch, Hans-Rudolf Meier
  • Patent number: 6271337
    Abstract: A new two-step process for the preparation and industrial manufacture of calixarenes is disclosed. In the first step, linear phenolic oligomers are prepared in a basic medium from an optionally substituted phenol and a formaldehyde source. The reaction mixture is then neutralized or acidified, and cyclization of the oligomers is brought about at higher temperatures in the same reaction medium which is made water free and optionally completed by higher boiling liquids. The process allows a definite control of the cyclic compounds to be synthesized. Furthermore, novel calixarene compounds are disclosed as well as an installation for carrying out the process on a laboratory or industrial scale.
    Type: Grant
    Filed: October 8, 1998
    Date of Patent: August 7, 2001
    Assignee: Fillger S.A.
    Inventors: Roger Lamartine, Isabelle Dumazet, Philippe Choquard, Arnold Marcillac, Francis Vocanson, Christian Duchamp
  • Patent number: 6201123
    Abstract: A catalyst composition for organic a symmetric synthesis is provided, which comprises: (A) a lanthanoid element ion; (B) a binaphthol, and (C) a nitrogen and/or phosphorus compound such as lutidine-N-oxide, 1,3-dimethyl-2-imidazolldinone, hexamethyl-phosphortriamide, triphenylphosphine oxide, tri(2-methylphenyl)phosphine oxide or tri(4-methylphenyl )phosphine oxide. Asymmetric epoxidation of an enone is conducted by allowing an enone to react with an oxidizing agent in the presence of the catalyst composition or a catalyst solution containing the catalyst composition.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: March 13, 2001
    Assignee: Techno Polymer Co., Ltd.
    Inventors: Kazuhiro Daikai, Masahiro Kamaura, Takeshi Hanamoto, Junji Inanaga
  • Patent number: 5959157
    Abstract: A process for making ethynylated, hydroxy-substituted biphenyl compounds comprising:a) halogenating 3,3'-dimethoxybiphenyl to form 2,2'-dihalo-5,5'-dimethoxybiphenyl;b) reacting the resulting 2,2'-dihalo-5,5'-dimethoxybiphenyl with a bromide-containing compound in a chlorinated solvent to form 2,2'-dihalo-5,5'-dihydroxybiphenyl;c) reacting the resulting 2,2'-dihalo-5,5'-dihydroxybiphenyl with a hydroxyl-containing compound in the presence of a protection catalyst to form 2,2'-dihalo-5,5'-bis(tetrahydropyranoxy)biphenyl;d) ethynylating the resulting 2,2'-dihalo-5,5'-bis(tetrahydropyranoxy)biphenyl with a compound of the formulaCuC.tbd.CR'wherein R' is comprised of an alkyl group having from about 1 to about 20 carbon atoms, an alkenyl group having from about 1 to about 20 carbon atoms, an aryl group, a heteroaryl group, or mixtures thereof to form 2,2'-bis(C.tbd.CR')-5,5'-bis(tetrahydropyranoxy)biphenyl; ande) hydrolyzing the resulting 2,2'-bis(C.tbd.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: September 28, 1999
    Assignee: Alliedsignal, Inc.
    Inventors: Kreisler Lau, Neil Hendricks, William Wan, Aaron Smith
  • Patent number: 5959158
    Abstract: Methods/systems for making a relatively high-purity bisphenol A product from phenol and acetone. Controlled turbulence is used to form bisphenol A adduct solids having improved physical properties. Phenol is separated from the bisphenol A product while inhibiting decomposition of bisphenol A.
    Type: Grant
    Filed: April 15, 1996
    Date of Patent: September 28, 1999
    Inventor: Ben Gammill
  • Patent number: 5889137
    Abstract: The present invention is directed to the formation of phenol alkylation polymers which release negligible phenol and formaldehyde emissions. The phenol aralkylation polymers of the present invention are derived from a phenolic monomer, at least one styrene derivative and an aryl diolefin. In addition to the phenolic monomer, styrene derivative and aryl diolefin, other reactants may be introduced to produce a product with particular properties.
    Type: Grant
    Filed: January 10, 1997
    Date of Patent: March 30, 1999
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: David A. Hutchings, Jeffrey L. Mills, Kenneth Bourlier
  • Patent number: 5874645
    Abstract: A process which includes the step of heating a compound of Formula (I): ##STR1## wherein R.sup.1 is a hydroxyphenyl group or a group of Formula (II): ##STR2## and R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently in each occurrence H or a C.sub.1-10 alkyl group; to a temperature in the range of from 100.degree. C. to 400.degree. C. under reaction conditions sufficient to form one or more 4,4'-dihydroxy-alpha-substituted stilbenes.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: February 23, 1999
    Assignee: The Dow Chemical Company
    Inventors: Anthony P. Haag, Thomas A. Chamberlin, Robert E. Hefner, Jr., David A. Carr
  • Patent number: 5773552
    Abstract: The present invention is directed to the formation of phenol alkylation polymers which release negligible phenol and formaldehyde emissions. The phenol aralkylation polymers of the present invention are derived from a phenolic monomer, at least one styrene derivative and an aryl diolefin. In addition to the phenolic monomer, styrene derivative and aryl diolefin, other reactants may be introduced to produce a product with particular properties.
    Type: Grant
    Filed: January 3, 1997
    Date of Patent: June 30, 1998
    Assignee: Georgia-Pacific Resins Inc.
    Inventors: David A. Hutchings, Jeffrey L. Mills, Kenneth Bourlier
  • Patent number: 5756642
    Abstract: The present invention is directed to the formation of phenol alkylation polymers which release negligible phenol and formaldehyde emissions. The phenol aralkylation polymers of the present invention are derived from a phenolic monomer, at least one styrene derivative and an aryl diolefin. In addition to the phenolic monomer, styrene derivative and aryl diolefin, other reactants may be introduced to produce a product with particular properties.
    Type: Grant
    Filed: January 3, 1997
    Date of Patent: May 26, 1998
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: David A. Hutchings, Jeffrey L. Mills, Kenneth Bourlier
  • Patent number: 5739259
    Abstract: The present invention is directed to the formation of phenol alkylation polymers which release negligible phenol and formaldehyde emissions. The phenol aralkylation polymers of the present invention are derived from a phenolic monomer, at least one styrene derivative and an aryl diolefin. In addition to the phenolic monomer, styrene derivative and aryl diolefin. In addition to the introduced to produce a product with particular properties.
    Type: Grant
    Filed: January 3, 1997
    Date of Patent: April 14, 1998
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: David A. Hutchings, Jeffrey L. Mills, Kenneth Bourlier
  • Patent number: 5723688
    Abstract: A process for preparing an adduct of a bisphenol with a phenolic compound comprising the following steps:a) reacting a carbonyl compound with a stoichiometric excess of a phenolic compound in the presence of an acidic cation exchange resin as a catalyst, to produce a product mixture containing a bisphenol, unreacted phenolic compound, unreacted carbonyl compound and water, andb) crystallizing an adduct of the bisphenol with the phenolic compound from the product mixture in a crystallization device in the presence of water and acetone.The product mixture obtained in step a) is not subjected to a distillation step before the product mixture enters the crystallization device and prior to the crystallization step b) the content of the carbonyl compound in the product mixture is controlled and, if necessary, carbonyl compound is added such that the total concentration of the carbonyl compound is from about 0.1 to about 8 percent, based on the total weight of the product mixture.
    Type: Grant
    Filed: November 15, 1995
    Date of Patent: March 3, 1998
    Assignee: The Dow Chemical Company
    Inventors: Emil Patrascu, Johann Wilhelm Frey, Hartwig Sendner
  • Patent number: 5674970
    Abstract: The present invention is directed to the formation of phenol alkylation polymers which release negligible phenol and formaldehyde emissions. The phenol aralkylation polymers of the present invention are derived from a phenolic monomer, at least one styrene derivative and an aryl diolefin. In addition to the phenolic monomer, styrene derivative and aryl diolefin, other reactants may be introduced to produce a product with particular properties.
    Type: Grant
    Filed: July 12, 1995
    Date of Patent: October 7, 1997
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: David A. Hutchings, Jeffrey L. Mills, Kenneth Bourlier
  • Patent number: 5612479
    Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: March 18, 1997
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5583267
    Abstract: In accordance with the present invention, tetraalkylbisphenols are prepared by biocatalytic dimerization of di-(lower alkyl)-substituted phenols in the presence of peroxidase enzyme and peroxide. Three reaction pathways to the desired diols are provided.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: December 10, 1996
    Assignee: Enzymol International, Inc.
    Inventors: Thurman M. Wheeler, Mark K. Morehart, Gregory Kaplan, Alexander R. Pokora
  • Patent number: 5475155
    Abstract: 4,4'-Dihydroxy-alpha-alkylstilbenes of high purity are prepared by reacting at a temperature of from about -20.degree. C. to about 20.degree. C. a mixture of (1) at least one alpha-haloketone, (2) at least one phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound, and (3) at least one strong protonic acid or Lewis acid; such that the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s) is from 0.1:1 to 1.9:1, and the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s):strong protonic acid or Lewis acid is from about 0.1:1:0.0026 to about 1.9:1:0.95. The high purity 4,4'-dihydroxy-alpha-alkylstilbenes are useful for the advancement of epoxy resins, for the preparation of phenoxy resins and for the preparation of epoxy resins.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: December 12, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Maria I. Villarreal, David A. Carr
  • Patent number: 5463140
    Abstract: A process for the condensation of an aldehyde or ketone starting material with a phenol, unsubstituted in the 4-position, comprises reacting the aldehyde or ketone starting material with the phenol in a reaction mixture in the presence of a soluble or insoluble mercaptosulfonic acid compound under conditions sufficient to bring about formation of a geminal bisphenolic moiety at each aldehyde or ketone moiety in the starting material. A miscible mercaptosulfonic acid compound is characterized by the formula(HS).sub.a -.theta.-(SO.sub.3 H).sub.bor a precursor thereof, wherein .theta. is an alkylene, cycloaliphatic, arylene, alkylenearylene, alkylenecycloaliphatic, alkylenearyl, heterocyclic or alkyleneheterocyclic residue.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: October 31, 1995
    Assignee: The Dow Chemical Company
    Inventors: Richard M. Wehmeyer, Marlin E. Walters, Emmett L. Tasset, Steven L. Brewster
  • Patent number: 5420363
    Abstract: An optically active tri-substituted methane compound having, as substituents, an aromatic ring group and a phenyl group having hydroxyl group at ortho or para position can be obtained by allowing a phenol compound unsubstituted at the ortho- or/and para-position to react with an optically active secondary carbinol compound having an aromatic ring group at the alpha-position in the presence of tri-substituted phosphine and diazodicarboxylate or diazodicarboxamide. These and other optically active tri-substituted methane compounds are useful as active ingredients for medicines or as intermediate compounds for preparing medicines.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: May 30, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsuru Shiraishi, Shoji Fukumoto
  • Patent number: 5420361
    Abstract: The production of cis-dihydrodiol compounds of the formula ##STR1## where n is 0 or 1 (preferably 0) by the microbial oxidation of a diphenylaceylene compound of the formula ##STR2## using a mutant of a Pseudomonas bacteria at 25.degree. to 35.degree. C. and pH 6-8 is disclosed. The cis-dihydrodiol compound is in turn treated with an aqueous solution of a base to produce a corresponding 3-hydroxydiphenylacetylene compound or with an aqueous solution of an acid to produce a corresponding 2-hydroxyacetylene compound.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: May 30, 1995
    Assignee: Bio-Technical Resources
    Inventor: Alan D. Grund
  • Patent number: 5414150
    Abstract: 4,4'-Dihydroxy-alpha-alkylstilbenes of high purity are prepared by reacting at a temperature of from about -20.degree. C. to about 20.degree. C. a mixture of (1) at least one alpha-haloketone, (2) at least one phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound, and (3) at least one strong protonic acid or Lewis acid; such that the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s) is from 0.1:1 to 1.9:1, and the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s):strong protonic acid or Lewis acid is from about 0.1:1:0.0026 to about 1.9:1:0.95. The high purity 4,4'-dihydroxy-alpha-alkylstilbenes are useful for the advancement of epoxy resins, for the preparation of phenoxy resins and for the preparation of epoxy resins.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Maria I. Villarreal, David A. Carr
  • Patent number: 5395985
    Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds to and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: March 7, 1995
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Fumio Toda
  • Patent number: 5364977
    Abstract: The present invention provides novel clathrate compounds using tetrakisphenols as host. The clathrate compounds are obtained easily and efficiently by reacting tetrakisphenols represented by the general formula [I] as host and various organic compounds such as alcohol, ether, ester, ketone, heterocyclic compounds containing nitrogen, essential oil, perfume and the like as guest under the condition of solvent-free or diluted with solvent if required. ##STR1## wherein X represents (CH.sub.2)n, n represents 0-3, and R.sup.1 and R.sup.2 represents each independently hydrogen atom, a lower alkyl group, a pheny group optionally having substituents, a halogen atom or a lower alcoxy group.The clathrate compounds specified in the present invention are useful in the technological field of selective separation, chemical stabilization, conversion to non-volatility, powder processing and the like.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: November 15, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Makoto Asai, Hiroshi Suzuki, Takako Ichikawa
  • Patent number: 5354913
    Abstract: An optically active tri-substituted methane compound having, as substituents, an aromatic ring group and a phenyl group having hydroxyl group at ortho or para position can be obtained by allowing a phenol compound unsubstituted at the ortho- or/and para-position to react with an optically active secondary carbinol compound having an aromatic ring group at the alpha-position in the presence of tri-substituted phosphine and diazodicarboxylate or diazodicarboxamide. These and other optically active tri-substituted methane compounds are useful as active ingredients for medicines or as intermediate compounds for preparing medicines.
    Type: Grant
    Filed: July 2, 1993
    Date of Patent: October 11, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsuru Shiraishi, Shoji Fukumoto
  • Patent number: 5340937
    Abstract: This invention includes an improved process of converting a phenate to a phenol using acid in which a two phase system having an aqueous phase containing phenate and an organic, phenol-containing, phase are present, the improvement comprising adding the acid to enter the aqueous phase while avoiding contact of the acid and phenol phase. Preferably, with sufficient mixing to substantially surround the organic phase with the aqueous phase. The addition is preferably accomplished by mixing the two phases sufficiently to disperse a small organic (phenol) phase in a (bulk) aqueous phase. Such a process conveniently comprises the steps of: (a) mixing a system containing an organic phenol-containing phase and an aqueous phase sufficiently to substantially surround regions of organic phase with aqueous phase; and (b) adding acid to the aqueous phase; and, optionally, (c) maintaining sufficient mixing to prevent contact of concentrated acid with the organic or phenol phase.
    Type: Grant
    Filed: January 8, 1993
    Date of Patent: August 23, 1994
    Inventors: Edward A. Fraini, George W. Tepera, Malcolm W. McClure
  • Patent number: 5331103
    Abstract: The present invention relates to a process for monohydroxylation of phenolic compounds which allows an increase in the amount of para isomer.The invention relates to a process for monohydroxylation of a phenolic compound having a hydrogen atom in the para position to the hydroxyl group, for the purpose of obtaining a dihydroxylated aromatic compound by reacting the initial phenolic compound with hydrogen peroxide in the presence of an effective amount of a strong acid and of a ketonic compound, said process being characterized by the fact that the reaction is carried out in the presence of an effective amount of a polar aprotic organic solvent with a basicity such that it has a "donor number" below 25.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: July 19, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • Patent number: 5319149
    Abstract: Bis[4-(4-hydroxyphenyl)-phenyl]alkanes, as illustrated by 2,2-bis[4-(4-hydroxyphenyl)-phenyl]propane, may be prepared by the reaction of a bisphenol A ester or a similar compound with a p-trialkyltin-substituted anisole, followed by demethylation with a Lewis acid such as boron tribromide. Polycarbonates prepared therefrom are ductile and have high glass transition temperatures.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: June 7, 1994
    Assignee: General Electric Company
    Inventors: John T. Bendler, John C. Schmidhauser, Kathryn L. Longley
  • Patent number: 5304688
    Abstract: A process for the preparation of bishydroxy aromatic compounds, such as 9,9-bis(4-hydroxyphenyl)fluorene, involving contacting a ketone, such as fluorenone, with phenol or substituted phenol in the presence of a mercaptan cocatalyst and a solid superacid catalyst of Hammett acid strength H.sub.0 greater than about -13.0. Solid superacid catalysts include the sulfates, sulfated oxides, sulfated oxyhydroxides, and sulfated oxysilicates of aluminum, tin, and the Group IVA metals, such as zirconium, as well as mixed metal oxides, such as tungsten-zirconium oxides. Isolated yields are high for 9,9-bis(4-hydroxyphenyl)fluorene.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: April 19, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, Muthiah N. Inbasekaran
  • Patent number: 5223602
    Abstract: This invention relates to naphthol aralkyl resins of the general formula (I) ##STR1## in which A is a naphthalene nucleus, R is hydrogen or methyl, and n is an integer from 0 to 15 and cured products thereof, which are highly heat- and moisture-resistant, possess excellent impact strength and other mechanical properties, and are useful for such applications as lamination, molding, casting, and adhesion.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 29, 1993
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Masashi Kaji, Takanori Aramaki, Norito Nakahara, Yasuharu Yamada
  • Patent number: 5196605
    Abstract: In a process for the preparation of 4,4'-dihydroxybiphenyl of high purity 4,4'-dibromobiphenyl is hydrolized in the presence of a copper compound catalyst, the insoluble materials comprising the catalyst is filtered off from the product mixture, 4,4'-dihydroxybiphenyl is precipitated by adjusting the pH and crude 4,4'-dihydroxybiphenyl separated from the product mixture is fractionally distilled to obtain substantially pure 4,4'-dihydroxybiphenyl.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: March 23, 1993
    Assignee: Bromine Compounds, Ltd.
    Inventors: Jakob Oren, Hugo Kesselman, Joshua Hermolin
  • Patent number: 5177258
    Abstract: Biaryl derivatives are produced by coupling an aryl halide in an aqueous alkaline solution in the presence of a palladium catalyst, using formic hydrazide as the reducing agent.
    Type: Grant
    Filed: May 21, 1992
    Date of Patent: January 5, 1993
    Assignee: Bromine Compounds, Ltd.
    Inventors: Abram Becker, Ariel A. Ewenson, Bertha Croitoru
  • Patent number: 5136114
    Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 5136110
    Abstract: The invention is a process for the preparation of triaromatic bisphenols reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene and a large portion of the yield is para isomer.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: August 4, 1992
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset