Phenolic Ether Formed Patents (Class 549/517)
  • Patent number: 9868683
    Abstract: Disclosed herein are compositions and methods of making phenolic compounds and phenolic resins. The resins include multifunctional epoxies, amino glycidyl derivatives, alkanoate derivatives, alkyl ether derivatives, and multi-functional amines prepared from hydroxymethyl derivatives of novolac resin.
    Type: Grant
    Filed: June 13, 2013
    Date of Patent: January 16, 2018
    Assignee: Empire Technology Development LLC
    Inventor: Georgius Abidal Adam
  • Patent number: 9527950
    Abstract: A process comprising: a) contacting a polyhydric phenol and an epihalohydrin in the presence of a catalyst under reaction conditions to form an organic feed comprising a bishalohydrin ether and a solvent; b) contacting the organic feed and an aqueous feed comprising an inorganic hydroxide in a reciprocating-plate column reactor under reaction conditions to form a dispersed aqueous phase and an organic product; and c) collecting the organic product comprising an epoxy resin, is disclosed.
    Type: Grant
    Filed: August 31, 2012
    Date of Patent: December 27, 2016
    Assignee: BLUE CUBE IP LLC
    Inventors: Thomas C. Young, William G. Worley, Robert M. Drake
  • Patent number: 9416218
    Abstract: The present application relates to a method for preparing epoxy resins from a mixture of epoxidized phenolic compounds, wherein said epoxidized phenolic compounds are obtained by the epoxidation of natural phenolic compounds selected from the group comprising simple phenol, acid-phenol, coumarin, naphthoquinone, stillbenoid, flavonoid, isoflavanoid, anthocyanin, condensed tannin and hydrolyzable tannin.
    Type: Grant
    Filed: May 27, 2010
    Date of Patent: August 16, 2016
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.), ECOLE NATIONALE SUPERIEURE DE CHIMIE DE MONTPELLIER
    Inventors: Bernard Boutevin, Sylvain Caillol, Carine Burguiere, Sylvie Rapior, Hélène Fulcrand, Hélène Nouailhas
  • Patent number: 9309209
    Abstract: Derivative of epichlorohydrin of natural origin, selected from the group consisting of glycidyl ethers presenting an epoxide equivalent weight higher than or equal to 50 g/equivalent and lower than or equal to 15000 g/equivalent, of glycidyl esters, of glycidyl amides, of glycidyl imides, of glycidyl amines, and of any mixture thereof, and of which the 14C mass content is such that the ratio 14C/12C is higher than 0.7 10?12.
    Type: Grant
    Filed: September 26, 2011
    Date of Patent: April 12, 2016
    Assignee: SOLVAY SA
    Inventor: Patrick Gilbeau
  • Patent number: 8742055
    Abstract: Use a modified, amine-functionalized anion exchange resin as a catalyst to produce a bishalohydrin ether and then dehydrohalogenate the bishalohydrin ether with an aqueous inorganic hydroxide mixture to yield a liquid epoxy resin.
    Type: Grant
    Filed: December 7, 2010
    Date of Patent: June 3, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Philip J. Carlberg, H. Robert Goltz, Leming Gu, William I. Harris, David H. West, William G. Worley, Thomas C. Young
  • Publication number: 20140066636
    Abstract: The present invention relates to an epoxy group-containing novel fluorene compound having a methallyl group at the end thereof represented by the following general formula (1): wherein R represents a hydrogen atom or a methyl group, which compound gives a compound excellent in regioselectivity at the time of hydrosilylation with a Si—H containing organosilicon compound, with a less formed amount of an internally added ? adduct, as compared with the conventionally known fluorene compound having an allyl group, so that heat resistance of the resulting organosilicon compound is expected to be improved whereby it is a useful compound.
    Type: Application
    Filed: August 5, 2013
    Publication date: March 6, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventor: Hideyoshi YANAGISAWA
  • Patent number: 8461286
    Abstract: A process for the production of liquid epoxy resins, including: contacting a polyhydric phenol and an epihalohydrin in the presence of an ionic catalyst to form a halohydrin intermediate reaction product; concurrently: reacting a portion of the halohydrin intermediate reaction product with an alkali hydroxide to form a solid salt suspended in a liquid mixture including a dehydrohalogenated product and unreacted halohydrin intermediate, wherein the alkali hydroxide is used at less than a stoichiometric amount; and removing water and epihalohydrin as a vapor from the reacting mixture; separating the solid salt from the liquid mixture; reacting at least a portion of the unreacted halohydrin intermediate with an alkali hydroxide in the presence of water to form an organic mixture including an epoxy resin and unreacted epihalohydrin and an aqueous solution including a salt; separating the aqueous mixture from the organic mixture; and separating the unreacted epihalohydrin from the liquid epoxy resin.
    Type: Grant
    Filed: March 24, 2009
    Date of Patent: June 11, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: Thomas C. Young, Clinton J. Boriack, Elwin G. Collier, Robert M. Drake, Joachim Drewing, Edward J. Kronenberger, Shuji Maeda, Paulo Alfonso Dos Santos Pereira, Andreas Tigges, Roland Werner, Mark S. Burkinshaw
  • Publication number: 20120283453
    Abstract: Use a modified, amine-functionalized anion exchange resin as a catalyst to produce a bishalohydrin ether and then dehydrohalogenate the bishalohydrin ether with an aqueous inorganic hydroxide mixture to yield a liquid epoxy resin.
    Type: Application
    Filed: December 7, 2010
    Publication date: November 8, 2012
    Applicant: Dow Global Technologies LLC
    Inventors: Philip J. Carlberg, H. Robert Goltz, Leming Gu, William I. Harris, David H. West, William G. Worley, Thomas C. Young
  • Publication number: 20120149807
    Abstract: A diepoxy compound represented by the formula (1) wherein R1, R2, R3 and R4 independently each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
    Type: Application
    Filed: August 26, 2010
    Publication date: June 14, 2012
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Taku Asaumi, Makoto Itagaki
  • Patent number: 8084650
    Abstract: Disclosed is an adamantane derivative which provides a cured product excellent in optical characteristics such as transparency and light resistance, long-term heat resistance, electrical characteristics such as and dielectric constant, and low water absorption. Also disclosed are a resin composition containing the adamantane derivative, a sealing agent for electronic circuits, optical electronic member, semiconductor device and copper-clad laminate all using the resin composition, and a radiation-sensitive resin composition which contains the above-mentioned adamantane derivative as a crosslinking agent.
    Type: Grant
    Filed: January 19, 2007
    Date of Patent: December 27, 2011
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Yasunari Okada, Hajime Ito, Hideki Yamane, Nobuaki Matsumoto
  • Publication number: 20110301366
    Abstract: A process comprising contacting a polyhydric phenol or a polyaliphatic alcohol with an epihalohydrin in the presence of a catalyst comprising a Schiff base metal complex is disclosed.
    Type: Application
    Filed: February 25, 2010
    Publication date: December 8, 2011
    Applicant: Dow Technologies LLC
    Inventors: Philip J. Carlberg, Thomas C. Young, Tina L. Arrowood, Ernesto Occhiello, Paul R. Elowe, Jason C. MacDonald
  • Patent number: 7332557
    Abstract: An epoxy resin represented by general formula (2), wherein R1-R4 indicate a hydrocarbon group of carbon number 1-6, n is 0 or integer of 1 or more and X is a bond or the following general formula wherein R5-R6 indicate a hydrogen atom or hydrocarbon group of carbon number 1-6, obtained by reacting an aromatic compound represented by general formula (1) and epihalohydrine, wherein R1-R4 and X are as identified herein, having molecular weight distribution comprising, content of n=0 component in the epoxy resin represented by general formula (2) is 60% or less and epoxy equivalent is 250 g/eq or over.
    Type: Grant
    Filed: January 13, 2004
    Date of Patent: February 19, 2008
    Assignee: Tohto Kasei Co., Ltd.
    Inventors: Shuya Shinohara, Masayoshi Hanabusa, Nobuhisa Saito, Hiroshi Nakanishi
  • Patent number: 7307128
    Abstract: The present invention relates to an epoxy compound, represented by a general formula (I), which is solid at ordinary temperature, has extremely low melt viscosity and has excellent curing property and which can provide a cured product which is excellent in mechanical strength, heat resistance, and moisture resistance. It also relates to a preparation method of the epoxy compound, an epoxy resin composition, and a cured product thereof. The epoxy compound is represented by the following general formula (I): (wherein R1-R10 each represent hydrogen atom or alkyl group having 1-6 carbon atoms, and n represents an integer of 0 or more).
    Type: Grant
    Filed: August 27, 2004
    Date of Patent: December 11, 2007
    Assignee: Japan Epoxy Resins Co., Ltd.
    Inventors: Atsuhito Hayakawa, Akihiro Itou
  • Patent number: 7304120
    Abstract: An epoxy compound, represented by a general formula (I) is obtained by reacting an anthrahydroquinone compound having a following general formula (II) with epihalohydrin. (wherein R1-R10 each represent hydrogen atom or alkyl group having 1-6 carbon atoms, and n represents an integer of 0 or more, and wherein A1, A2 each represent hydrogen atom or alkali metal atom, R1-R10 each represent hydrogen atom or alkyl group having 1-6 carbon atoms.
    Type: Grant
    Filed: January 26, 2007
    Date of Patent: December 4, 2007
    Assignee: Japan Epoxy Resins Co., Ltd.
    Inventors: Atsuhito Hayakawa, Akihiro Itou
  • Patent number: 7265232
    Abstract: A process for producing a glycidyl ether and an optically active compound thereof with high yield and an optically high purity comprising reacting an alcohol with epihalohydrin in a base to thereby produce a glycidyl ether, the reaction performed in a two-layer system of a nonaqueous organic solvent and an aqueous solvent.
    Type: Grant
    Filed: May 29, 2003
    Date of Patent: September 4, 2007
    Assignee: Daiso Co., Ltd.
    Inventors: Yoshiro Furukawa, Yasushi Miki, Keisuke Yaegashi
  • Patent number: 7169944
    Abstract: An optically active epoxyenone derivative of the following formula (1): wherein R1 is a methyl group, an ethyl group or a C3-10 branched, linear or cyclic alkyl group, and R2 is a phenyl group, a substituted phenyl group or a tert-butyl group.
    Type: Grant
    Filed: September 23, 2003
    Date of Patent: January 30, 2007
    Assignee: Tosoh Corporation
    Inventors: Takumi Kagawa, Takeshi Kambara, Hideo Sakka, Manabu Yanase
  • Patent number: 7078414
    Abstract: The present invention relates to 3-guanidinocarbonyl-1-heteroaryl-pyrrole derivatives of formula (I) wherein R1 to R3 and Ar are as defined herein, pharmaceutical compositions comprising such derivatives, methods of treatment comprising administering such derivatives, and processes for their preparation
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: July 18, 2006
    Assignee: Sanofi-Aventis Deutschland GmbH
    Inventors: Heinz-Werner Kleemann, Pascal Desmazeau, Jean-Christophe Carry, Baptiste Ronan, Serge Mignani, Jean Bououerel, Arielle Genevois-Borella
  • Patent number: 7067233
    Abstract: A compound including an epoxy group that has a heat curing property and a chalcone group that has a radiation curing property is represented by the following formula: wherein n is an integer from 1 to 10,000, and each of R1, R2, R3, R4, R5, R6, R7 and R8 is selected from a group consisting of a hydrogen atom, alkyl group, alkoxy group, halogen atom and nitro group. The compound has a high curing efficiency. A photoresist composition including the compound above substantially prevents the formation of remnant in a photoresist pattern used in the manufacturing of a color filter. In addition, the color filter pattern that is formed using the photoresist composition has high color reproductivity and brightness.
    Type: Grant
    Filed: March 24, 2004
    Date of Patent: June 27, 2006
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Yoon-Ho Kang, Dong-Ho Bae, Jang-Sub Kim
  • Patent number: 6812318
    Abstract: The object of the present invention is to provide an epoxy resin and epoxy resin composition having a low viscosity which can afford a cured product having an excellent heat resistance. The present invention is characterized by using an epoxy resin which is obtained by reacting 5-methylresorcin with epihalohydrin in the presence of alkali metal hydroxide.
    Type: Grant
    Filed: July 18, 2002
    Date of Patent: November 2, 2004
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yasumasa Akatsuka, Koji Nakayama, Katsuhiko Oshimi, Syouichi Tomida
  • Patent number: 6693149
    Abstract: A process for preparing an epoxy group-containing curable polyphenylene ether (PPE) resin. The process involves introducing an epoxy group-containing functional group to the terminal end of PPE (Mn>3000) by modifying the hydroxy and ester groups on the terminal end. Thus, a curable PPE resin (Mn>3000) including an epoxy group on the terminal end can be obtained. The modified PPE resin contains epoxy groups and has high glass transition temperature.
    Type: Grant
    Filed: April 25, 2002
    Date of Patent: February 17, 2004
    Assignee: Industrial Technology Research Institute
    Inventors: Meng-Song Yin, Chien-Ting Lin, Hung-Chou Kang
  • Patent number: 6548620
    Abstract: The present invention provides a tetramethylbiphenyl type high performance epoxy resin composition and a curable epoxy resin composition containing the epoxy resin, useful in electrical and electronic fields and the like. The tetramethylbiphenyl type epoxy resin composition comprises an epoxy resin composition obtained by reacting 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl and an epihalohydrin in the presence of an alkali metal compound. The composition has a content of tetramethyldiphenoquinone of 0.5% by weight or less and a content of a glycidyl compound represented by the following structural formula (1): of 0.5% by weight or less. The curable epoxy resin composition contains the epoxy resin composition and a hardener for the epoxy resin.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: April 15, 2003
    Assignee: Japan Epoxy Resins Co., Ltd.
    Inventor: Yasuyuki Murata
  • Patent number: 6531549
    Abstract: A crystallized epoxy resin which is easy to blend with a hardener or the like is a crystallized product of an epoxy resin derived from 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl and an epihalohydrin, and the ratio of an endotherm between 50° C. and 130° C. to an endotherm between 80° C. and 125° C., measured by raising the temperature at a rate of 10° C. per minute using a DSC device, is 1.03 or more.
    Type: Grant
    Filed: December 12, 2001
    Date of Patent: March 11, 2003
    Assignee: Japan Epoxy Resins Co., Ltd.
    Inventors: Yasuyuki Murata, Masayuki Tsutsumi, Kiyotaka Ikebata, Ken Tanaka
  • Patent number: 6407150
    Abstract: A process for producing phenol resin having good color tone, which process comprises reacting hydroxyl group-containing aromatic compound and unsaturated cyclic hydrocarbon under the condition that the moisture is 100 ppm or less and the concentration of Friedel-Crafts catalyst is 0.07 mass % or less in a reaction system and a process for producing epoxy resin having good color tone, which process comprises reacting the obtained phenol resin and epihalohydrin in the presence of base catalyst, removing remaining catalyst and further removing unreacted epihalohydrin.
    Type: Grant
    Filed: August 10, 2000
    Date of Patent: June 18, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Satoshi Mori, Fumiaki Oshimi, Masato Hattori
  • Patent number: 6392064
    Abstract: The present invention relates to a method of synthesizing glycidyl ether compounds without the addition of solvent. In particular, the present invention provides the improved preparation of the glycidyl ethers by using fatty alcohols with epichlorohydrin in the presence of alkali metal hydroxide and phase-transfer catalysts in the appropriate molar ratios of them without water and organic solvents.
    Type: Grant
    Filed: March 29, 2001
    Date of Patent: May 21, 2002
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Byung Min Lee, Ho-Cheol Kang, Jong-mok Park, Jung Ho Yoon
  • Publication number: 20020004605
    Abstract: The present invention relates to a method of synthesizing glycidyl ether compounds without the addition of solvent. In particular, the present invention provides the improved preparation of the glycidyl ethers by using fatty alcohols with epichlorohydrin in the presence of alkali metal hydroxide and phase-transfer catalysts in the appropriate molar ratios of them without water and organic solvents.
    Type: Application
    Filed: March 29, 2001
    Publication date: January 10, 2002
    Applicant: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY
    Inventors: Byung Min Lee, Ho-Cheol Kang, Jong-mok Park, Jung Ho Yoon
  • Patent number: 6326393
    Abstract: Compounds of Formula I are disclosed as inhibitors having activity against the aspartyl proteases, plasmepsin and cathepsin D. The compounds are therefore useful for treatment of diseases such as malaria and Alzheimer's disease. In preferred compounds of Formula I, Y is an dialkoxyphosphonate, or &agr;-hydroxyamide group and Z is an acyl or &agr;-ketocarbamate functionality. Intermediates in the solid phase synthesis of compounds of Formula I, in which compounds are attached to a solid support, are also disclosed.
    Type: Grant
    Filed: June 20, 2000
    Date of Patent: December 4, 2001
    Assignee: Pharmacopeia, Inc.
    Inventors: Carolyn DiIanni Carroll, Roland Ellwood Dolle, III, Yvonne Class Shimshock, Timothee Felix Herpin
  • Patent number: 6222054
    Abstract: The method for producing an epoxy resin involving the steps of: reacting at least one phenol compound with at least one aldehyde compound to obtain a novolak resin; storing the novolak resin in a molten state in an inert gas atmosphere; feeding the stored novolak resin into an epoxidation reactor; and reacting the stored novolak resin with an epihalohydrin compound, which prevents generation of dust improving the working environment, increases production efficiency reducing production cost, and further suppresses quality degradation such as coloring of the epoxy resin.
    Type: Grant
    Filed: November 23, 1999
    Date of Patent: April 24, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Morimoto, Hideshi Sakamoto, Masakazu Takahashi
  • Patent number: 6087512
    Abstract: A process for preparation of a glycidyl ether which is characrelized in reacting an epoxy compound of the formula ##STR1## wherein X is halogen or sulfonyloxy in the presence of a fluoride salt, with an alcohol. According to the above method, glycigyl ethers or their optically active compounds important as intermediates for synthesis of medicines are easily obtained in good yield and especially the optically active compounds are obtained with highly optical purity.
    Type: Grant
    Filed: April 29, 1999
    Date of Patent: July 11, 2000
    Assignee: Daiso Co., Ltd.
    Inventors: Yoshiro Furukawa, Kazuhiro Kitaori, Tetsuya Yanagimoto, Masafumi Mikami, Hiroshi Yoshimoto, Junzo Otera
  • Patent number: 6084039
    Abstract: An epoxy resin which is useful as adhesives, resins for coatings, encapsulants, resins for a lamination board, casting materials, molding compounds, and electric insulators, and which can provide a cured resin having excellent heat resistance and moisture resistance is provided which comprises (A) an epoxy resin containing a trisepoxy compound represented by general formula (I), and (B) a curing agent for an epoxy resin, ##STR1## wherein R.sub.1 is a methyl group, n is an integer of 0 to 2, and Ar is a group selected from general formula (II) ##STR2## wherein R.sub.2 and R.sub.3 are an alkyl group having a carbon number of 1 to 6, an alkoxy group having a carbon number of 1 to 6, or a halogen atom, and m and p are an integer of 0 to 2.
    Type: Grant
    Filed: March 3, 1998
    Date of Patent: July 4, 2000
    Assignee: Shell Oil Company
    Inventors: Mareki Miura, Yoshinobu Ohnuma
  • Patent number: 5955551
    Abstract: The present invention relates to polyglycidyl ether compounds containing at least three mono- or divalent radicals A of the general formula wherein R.sub.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: September 21, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Chi-Wen Frank Cheng, Mark Bryant
  • Patent number: 5948923
    Abstract: A number of new phenolepoxy resins are prepared by reacting polyphenol, epihalohydrin and imidazole in a homogeneous reaction medium.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: September 7, 1999
    Assignee: Industrial Technology Research Institute
    Inventors: Kung-Lung Cheng, Woan-Shiow Tzeng, Shu-Chen Lin
  • Patent number: 5945501
    Abstract: A bis(methoxymethyl)biphenyl having the formula (I): ##STR1## which is capable of producing by a dehalogenating coupling of a halogenated methoxymethylbenzene and which is useful as an intermediate for a phenol novolak condensate, an epoxy resin curing agent, an epoxy resin composition, or a phenol resin composition.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: August 31, 1999
    Assignees: UBE Industries, Ltd., Meiwa Plastic Industries
    Inventors: Katuhiko Okazaki, Mikito Kashima, Yumiki Noda, Hiroshi Jibiki, Takashi Honma
  • Patent number: 5880246
    Abstract: A polyepoxy composition comprising a trisepoxide represented by general formula (I) described below which is well-balanced between thermal stability and water resistance is provided. ##STR1## In the formula, R represents a methyl group, X represents an alkyl group having a carbon number of 1 to 6, an alkoxy group having a carbon number of 1 to 6, or a halogen atom, which may be identical or different, respectively, Y represents a hydrogen atom or a methyl group, and m and n represent an integer of 0 to 2.
    Type: Grant
    Filed: July 8, 1997
    Date of Patent: March 9, 1999
    Assignee: Shell Oil Company
    Inventors: Mareki Miura, Yoshinobu Ohnuma
  • Patent number: 5844062
    Abstract: A process for preparing phenolepoxy resin represented by the following formula: ##STR1## wherein: (a) R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which can be the same or different, are hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; (b) R.sup.5 and R.sup.6, which can be the same or different, are hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; ##STR2## (c) R.sup.7 is hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; (d) R.sup.8 and R.sup.9, which can be the same of different, are hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; and (e) n is an integer of 0 or 1.
    Type: Grant
    Filed: April 29, 1997
    Date of Patent: December 1, 1998
    Assignee: Industrial Technology Research Institute
    Inventors: Kung-Lung Cheng, Woan-Shiow Tzeng, Shu-Chen Lin
  • Patent number: 5777007
    Abstract: Brominated p-cumylphenol represented by the formula (1) described hereinafter and derivative thereof represented by the formula (2) described hereinabove, process for the preparation of the same, and flame-retardant resin compositions containing the same, are disclosed. Those compounds are useful flame retardant, and can be blended with various thermosetting resins or thermoplastic resins to obtain flame retardant resin compositions.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: July 7, 1998
    Assignee: Tosoh Corporation
    Inventors: Takumi Kagawa, Norihisa Kondo, Noriyuki Kasai, Hideo Sakka
  • Patent number: 5650412
    Abstract: Compounds of formula ##STR1## are HIV protease inhibitors. These compounds are useful in the prevention or treatment of infection by HIV and in the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
    Type: Grant
    Filed: October 26, 1995
    Date of Patent: July 22, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Byeong Moon Kim, Joseph P. Vacca
  • Patent number: 5606006
    Abstract: Cure of a novel trisepoxy resin-based composition provides a thermoset having high Tg, low dielectric constant, low water absorption and good flexural strength.
    Type: Grant
    Filed: April 8, 1996
    Date of Patent: February 25, 1997
    Assignee: Shell Oil Company
    Inventor: Pen-Chung Wang
  • Patent number: 5439989
    Abstract: Macrocyclic epoxy resins comprising at least one compound of the formula (I) ##STR1## wherein n is an integer from 3 to 10.R.sup.1 and R.sup.3 are either the same or different and are selected from hydrogen, hydroxyl, alkoxy, allyloxy and epoxypropyloxy (glycidyloxy);R.sup.2 is selected from hydrogen, arylakalkyl optionally substituted with halogen, alkyl optionally substituted with halogen, and aryl optionally substituted with halogen;R.sup.4 is selected from hydrogen, alkyl optionally substituted with halogen, arylalkyl optionally substituted with alkyl or halogen, and aryl optionally substituted with halogen;R.sup.5 is selected from hydrogen, aryl and alkyl; with the proviso that the resin contains on average at least one epoxy group per molecule.
    Type: Grant
    Filed: May 3, 1993
    Date of Patent: August 8, 1995
    Assignee: Commonwealth Scientific & Industrial Research Organisation
    Inventors: Trevor C. Morton, Jonathan H. Hodgkin, Buu N. Dao
  • Patent number: 5359097
    Abstract: A process is provided for preparation of a glycidyl ether represented by the general formula ##STR1## wherein A represents an aryl group optionally having a substituent or a heteroaryl group optionally having a substituent, and the carbon atom marked with * is an asymmetric carbon,which comprises reacting an aryl alcohol represented by the general formulaA--OH (I)wherein A is as defined above,with an epihalohydrin in the presence of a quaternary ammonium salt; and, if necessary, further treating the reaction product with a base. According to the present process, it is possible to prepare by simple procedures and in a high optical purity glycidyl ethers of the above formula (II) useful as an intermediate for preparation of medicines, particularly medicines having .beta.-adrenoreceptor blocking action or the like.
    Type: Grant
    Filed: August 22, 1990
    Date of Patent: October 25, 1994
    Assignee: Kowa Company Ltd.
    Inventors: Kiyoshi Kawamura, Tomio Ota
  • Patent number: 5310955
    Abstract: A vertical reactor system having a plurality of substantially vertically aligned reaction compartments one on top of the other, the reactant materials (and catalyst and solvent, if desired), flowable from a first top compartment through intermediate compartments, if any, to a bottom compartment from which a desired product of a reaction of the reactant materials is withdrawn, the compartments having inlets for the addition of additional reactants, catalysts, or solvents and outlets for withdrawing by-products, vapors, and water from any compartment, and processes for producing products using such a system. In one embodiment the product is a liquid epoxy resin. Stirring impellers may be provided in any compartment. A liquid seal may be provided on a shaft for the impellers and, in one embodiment the seals in each compartment may be elevated above the liquid in the compartments.
    Type: Grant
    Filed: August 16, 1993
    Date of Patent: May 10, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert P. Shirtum, Walter L. Wernli, David D. McCoy
  • Patent number: 5304624
    Abstract: A method for preparing 1,1,2,2-tetrakis(4-hydroxy-3,5-dimethylphenyl)ethane (TKXE) comprising subjecting two molecules of bis(3,5-dimethyl-4-hydroxyphenyl) methane to dehydration-condensation under oxidizing conditions, an epoxy resin prepared by epoxidating TKXE obtained by the method and an epoxy resin composition comprising TKXE obtained by the method as a hardener and an epoxy resin as well as methods for preparing the resin and composition. The method makes it possible to prepare highly pure TKXE in the form of crystals. Moreover, the epoxy resin and the epoxy resin composition can provide hardened products excellent in physical properties such as heat resistance and mechanical strength.
    Type: Grant
    Filed: July 9, 1992
    Date of Patent: April 19, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Naru Koike, Shigeru Iimuro, Mizuo Ito
  • Patent number: 5290958
    Abstract: A phase transfer catalytic process for the preparation of epoxide and halohydrin intermediates, which can be subsequently and directly reacted with isopropylamine to produce beta-adrenergic antagonists such as atenolol, propanolol and their derivatives. In the process disclosed in the present invention, quaternary ammonium salts of high alkyl groups or tertiary ammonium salts of lower alkyl groups are used as catalyst in the phase transfer catalytic oxygenated-alkylation reaction between an aromatic alcohol such as p-hydroxyphenyl acetamide (for the production of atenolol) or .alpha.-naphthol (for the production of propranolol) and epichlorohydrin to yield epoxide and halohydrin intermediates. The quaternary ammonium salts of high alkyl groups are represented by the following formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are C.sub.1 to C.sub.20 alkyl groups and at least one of the R.sub.1, R.sub.2, R.sub.3, or R.sub.4 is a C.sub.9 to C.sub.20 alkyl group, and X is a halide group.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: March 1, 1994
    Assignee: Industrial Technology Research Institute
    Inventors: Shyue-Ming Jang, Tian-Shy Shieh
  • Patent number: 5278260
    Abstract: A process for the preparation of epoxy resins having a specific reproducible content of .alpha.-glycol groups, which process comprises adding at least 0.0085 mol of glycidol or glycidol precursor compound per hydroxy-equivalent of a phenolic compound A which contains 2, 3 or 4 phenolic hydroxyl groups during the reaction of said phenolic compound A with an epihalohydrin which is unsubstituted or substituted in 2- or 3-position by C.sub.1 -C.sub.4 alkyl. The products may be used for surface protection.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: January 11, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Schaffner, Dimiter Hadjistamov
  • Patent number: 5245057
    Abstract: A continuous horizontal reactor system and process for employing such a system. In one embodiment, a reactor system having a cylindrical multi-compartment vessel, the compartments intercommunicating via a common overhead space or separated spaces from which vapor with reaction product or by-products may be removed, and from which liquid effluent with reaction products or by-products may be removed and reactants and catalyst flowable into each compartment and agitators in each compartment. Such a reactor system for producing liquid epoxy resins. Processes using such a reactor to produce reaction products, e.g. liquid epoxy resins.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: September 14, 1993
    Assignee: The Dow Chemical Company
    Inventor: Robert P. Shirtum
  • 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: 5239093
    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 or H.sup.+ or a hydronium 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 or diol and epichlorohydrin in the presence of the foregoing catalyst, followed by ring closure employing an alkali to produce a mono- or polyglycidyl ether.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: August 24, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Chi-Wen F. Cheng
  • Patent number: 5218060
    Abstract: An epoxide resin having the formula I: ##STR1## in which R.sup.1 to R.sup.4 are the same or different and each is hydrogen or C.sub.1 -C.sub.12 alkyl; R.sup.5 to R.sup.12 are the same or different and each is C.sub.1 -C.sub.12 alkyl or alkenyl or the glycidyl residue such that at least two R.sup.5 to R.sup.12 groups are glycidyl residues; and R.sup.13 to R.sup.20 are the same or different and are hydrogen, halogen C.sub.1 -C.sub.12 alkyl or alkenyl.
    Type: Grant
    Filed: February 7, 1992
    Date of Patent: June 8, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: William M. Rolfe, Michael R. Thoseby
  • Patent number: 5155202
    Abstract: A phenolic novolak resin comprising a compound represented by the general formula [I]: ##STR1## wherein X is H or ##STR2## R is an alkyl group having 1 to 4 carbon atoms, and n is 1 to 10, particularly a phenolic novolak epoxy resin, and material, and a cured substance therefrom, and a process for producing the resin are disclosed. This resin is excellent in heat resistance and in reluctance to absorb water as compared with conventional phenolic resins, and useful in sealing electronic parts, molding, and laminating.
    Type: Grant
    Filed: February 6, 1991
    Date of Patent: October 13, 1992
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hiromi Morita, Kazuyuki Murata, Ichiro Kimura, Susumu Nagao
  • Patent number: 5130482
    Abstract: Improved process for producing an optically active atenolol useful as a .beta.-adrenergic blocker for the treatment of angina pectoris, arrhythmia and hypertension, which comprising reacting a phenol compound with an optically active epihalohydrin to give an intermediate, optically active glycidyl ether compound, followed by reacting the intermediate with isopropylamine, and purification method of the optically active atenolol in high yield by means of forming a salt of atenolol with a Bronsted's acid whereby the salt of optically active atenolol having high optical purity can be separated from the salt of racemic atenolol by solid-liquid separation method.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: July 14, 1992
    Assignee: Daiso Company, Ltd.
    Inventors: Yoshikazu Takehira, Nobuaki Saragai, Kazuhiro Kitaori
  • Patent number: H1439
    Abstract: The performance of epoxy resins in several end-uses is enhanced by the presence of small quantities of hydrolyzed resin terminated by .alpha.-glycol groups. The invention is a process in which a mixture that contains liquid epoxy resin and water is reacted at elevated temperatures in order to hydrolyze epoxy groups into .alpha.-glycol groups, characterized in that: (1) the reaction temperature is between 130.degree. C. and 200.degree. C; (2) the reaction mixture contains 0.5 and 10 parts water per 100 parts resin by weight; and (3) the mixture contains 0 to 1 weight percent organic solvents and 0 to 100 ppm each of: organic acids, organic diacids, phosphonium compounds, and alkali or alkaline earth metals and their salts. The process raises the level of .alpha.-glycol groups in the resin, but uses no solvents or catalysts, so that it is easy to clean up the resulting resin.
    Type: Grant
    Filed: October 18, 1993
    Date of Patent: May 2, 1995
    Assignee: The Dow Chemical Company
    Inventor: Thomas J. Hairston