Phenolic Ether Formed Patents (Class 549/517)
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Patent number: 9868683Abstract: 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: GrantFiled: June 13, 2013Date of Patent: January 16, 2018Assignee: Empire Technology Development LLCInventor: Georgius Abidal Adam
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Patent number: 9527950Abstract: 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: GrantFiled: August 31, 2012Date of Patent: December 27, 2016Assignee: BLUE CUBE IP LLCInventors: Thomas C. Young, William G. Worley, Robert M. Drake
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Patent number: 9416218Abstract: 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: GrantFiled: May 27, 2010Date of Patent: August 16, 2016Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.), ECOLE NATIONALE SUPERIEURE DE CHIMIE DE MONTPELLIERInventors: Bernard Boutevin, Sylvain Caillol, Carine Burguiere, Sylvie Rapior, Hélène Fulcrand, Hélène Nouailhas
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Patent number: 9309209Abstract: 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: GrantFiled: September 26, 2011Date of Patent: April 12, 2016Assignee: SOLVAY SAInventor: Patrick Gilbeau
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Patent number: 8742055Abstract: 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: GrantFiled: December 7, 2010Date of Patent: June 3, 2014Assignee: Dow Global Technologies LLCInventors: Philip J. Carlberg, H. Robert Goltz, Leming Gu, William I. Harris, David H. West, William G. Worley, Thomas C. Young
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Publication number: 20140066636Abstract: 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: ApplicationFiled: August 5, 2013Publication date: March 6, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventor: Hideyoshi YANAGISAWA
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Patent number: 8461286Abstract: 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: GrantFiled: March 24, 2009Date of Patent: June 11, 2013Assignee: Dow Global Technologies LLCInventors: 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
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Publication number: 20120283453Abstract: 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: ApplicationFiled: December 7, 2010Publication date: November 8, 2012Applicant: Dow Global Technologies LLCInventors: Philip J. Carlberg, H. Robert Goltz, Leming Gu, William I. Harris, David H. West, William G. Worley, Thomas C. Young
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Publication number: 20120149807Abstract: 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: ApplicationFiled: August 26, 2010Publication date: June 14, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Taku Asaumi, Makoto Itagaki
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Patent number: 8084650Abstract: 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: GrantFiled: January 19, 2007Date of Patent: December 27, 2011Assignee: Idemitsu Kosan Co., Ltd.Inventors: Yasunari Okada, Hajime Ito, Hideki Yamane, Nobuaki Matsumoto
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Publication number: 20110301366Abstract: 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: ApplicationFiled: February 25, 2010Publication date: December 8, 2011Applicant: Dow Technologies LLCInventors: Philip J. Carlberg, Thomas C. Young, Tina L. Arrowood, Ernesto Occhiello, Paul R. Elowe, Jason C. MacDonald
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Patent number: 7332557Abstract: 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: GrantFiled: January 13, 2004Date of Patent: February 19, 2008Assignee: Tohto Kasei Co., Ltd.Inventors: Shuya Shinohara, Masayoshi Hanabusa, Nobuhisa Saito, Hiroshi Nakanishi
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Patent number: 7307128Abstract: 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: GrantFiled: August 27, 2004Date of Patent: December 11, 2007Assignee: Japan Epoxy Resins Co., Ltd.Inventors: Atsuhito Hayakawa, Akihiro Itou
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Patent number: 7304120Abstract: 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: GrantFiled: January 26, 2007Date of Patent: December 4, 2007Assignee: Japan Epoxy Resins Co., Ltd.Inventors: Atsuhito Hayakawa, Akihiro Itou
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Patent number: 7265232Abstract: 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: GrantFiled: May 29, 2003Date of Patent: September 4, 2007Assignee: Daiso Co., Ltd.Inventors: Yoshiro Furukawa, Yasushi Miki, Keisuke Yaegashi
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Patent number: 7169944Abstract: 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: GrantFiled: September 23, 2003Date of Patent: January 30, 2007Assignee: Tosoh CorporationInventors: Takumi Kagawa, Takeshi Kambara, Hideo Sakka, Manabu Yanase
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Patent number: 7078414Abstract: 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 preparationType: GrantFiled: December 23, 2003Date of Patent: July 18, 2006Assignee: Sanofi-Aventis Deutschland GmbHInventors: Heinz-Werner Kleemann, Pascal Desmazeau, Jean-Christophe Carry, Baptiste Ronan, Serge Mignani, Jean Bououerel, Arielle Genevois-Borella
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Patent number: 7067233Abstract: 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: GrantFiled: March 24, 2004Date of Patent: June 27, 2006Assignee: Samsung Electronics Co., Ltd.Inventors: Yoon-Ho Kang, Dong-Ho Bae, Jang-Sub Kim
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Patent number: 6812318Abstract: 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: GrantFiled: July 18, 2002Date of Patent: November 2, 2004Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yasumasa Akatsuka, Koji Nakayama, Katsuhiko Oshimi, Syouichi Tomida
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Patent number: 6693149Abstract: 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: GrantFiled: April 25, 2002Date of Patent: February 17, 2004Assignee: Industrial Technology Research InstituteInventors: Meng-Song Yin, Chien-Ting Lin, Hung-Chou Kang
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Patent number: 6548620Abstract: 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: GrantFiled: October 16, 2001Date of Patent: April 15, 2003Assignee: Japan Epoxy Resins Co., Ltd.Inventor: Yasuyuki Murata
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Patent number: 6531549Abstract: 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: GrantFiled: December 12, 2001Date of Patent: March 11, 2003Assignee: Japan Epoxy Resins Co., Ltd.Inventors: Yasuyuki Murata, Masayuki Tsutsumi, Kiyotaka Ikebata, Ken Tanaka
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Patent number: 6407150Abstract: 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: GrantFiled: August 10, 2000Date of Patent: June 18, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Satoshi Mori, Fumiaki Oshimi, Masato Hattori
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Patent number: 6392064Abstract: 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: GrantFiled: March 29, 2001Date of Patent: May 21, 2002Assignee: Korea Research Institute of Chemical TechnologyInventors: Byung Min Lee, Ho-Cheol Kang, Jong-mok Park, Jung Ho Yoon
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Publication number: 20020004605Abstract: 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: ApplicationFiled: March 29, 2001Publication date: January 10, 2002Applicant: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGYInventors: Byung Min Lee, Ho-Cheol Kang, Jong-mok Park, Jung Ho Yoon
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Patent number: 6326393Abstract: 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: GrantFiled: June 20, 2000Date of Patent: December 4, 2001Assignee: Pharmacopeia, Inc.Inventors: Carolyn DiIanni Carroll, Roland Ellwood Dolle, III, Yvonne Class Shimshock, Timothee Felix Herpin
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Patent number: 6222054Abstract: 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: GrantFiled: November 23, 1999Date of Patent: April 24, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Morimoto, Hideshi Sakamoto, Masakazu Takahashi
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Patent number: 6087512Abstract: 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: GrantFiled: April 29, 1999Date of Patent: July 11, 2000Assignee: Daiso Co., Ltd.Inventors: Yoshiro Furukawa, Kazuhiro Kitaori, Tetsuya Yanagimoto, Masafumi Mikami, Hiroshi Yoshimoto, Junzo Otera
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Patent number: 6084039Abstract: 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: GrantFiled: March 3, 1998Date of Patent: July 4, 2000Assignee: Shell Oil CompanyInventors: Mareki Miura, Yoshinobu Ohnuma
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Patent number: 5955551Abstract: 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: GrantFiled: August 6, 1997Date of Patent: September 21, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Chi-Wen Frank Cheng, Mark Bryant
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Patent number: 5948923Abstract: A number of new phenolepoxy resins are prepared by reacting polyphenol, epihalohydrin and imidazole in a homogeneous reaction medium.Type: GrantFiled: October 30, 1998Date of Patent: September 7, 1999Assignee: Industrial Technology Research InstituteInventors: Kung-Lung Cheng, Woan-Shiow Tzeng, Shu-Chen Lin
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Patent number: 5945501Abstract: 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: GrantFiled: December 6, 1996Date of Patent: August 31, 1999Assignees: UBE Industries, Ltd., Meiwa Plastic IndustriesInventors: Katuhiko Okazaki, Mikito Kashima, Yumiki Noda, Hiroshi Jibiki, Takashi Honma
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Patent number: 5880246Abstract: 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: GrantFiled: July 8, 1997Date of Patent: March 9, 1999Assignee: Shell Oil CompanyInventors: Mareki Miura, Yoshinobu Ohnuma
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Patent number: 5844062Abstract: 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: GrantFiled: April 29, 1997Date of Patent: December 1, 1998Assignee: Industrial Technology Research InstituteInventors: Kung-Lung Cheng, Woan-Shiow Tzeng, Shu-Chen Lin
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Patent number: 5777007Abstract: 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: GrantFiled: March 10, 1997Date of Patent: July 7, 1998Assignee: Tosoh CorporationInventors: Takumi Kagawa, Norihisa Kondo, Noriyuki Kasai, Hideo Sakka
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Patent number: 5650412Abstract: 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: GrantFiled: October 26, 1995Date of Patent: July 22, 1997Assignee: Merck & Co., Inc.Inventors: Byeong Moon Kim, Joseph P. Vacca
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Patent number: 5606006Abstract: 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: GrantFiled: April 8, 1996Date of Patent: February 25, 1997Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 5439989Abstract: 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: GrantFiled: May 3, 1993Date of Patent: August 8, 1995Assignee: Commonwealth Scientific & Industrial Research OrganisationInventors: Trevor C. Morton, Jonathan H. Hodgkin, Buu N. Dao
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Patent number: 5359097Abstract: 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: GrantFiled: August 22, 1990Date of Patent: October 25, 1994Assignee: Kowa Company Ltd.Inventors: Kiyoshi Kawamura, Tomio Ota
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Patent number: 5310955Abstract: 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: GrantFiled: August 16, 1993Date of Patent: May 10, 1994Assignee: The Dow Chemical CompanyInventors: Robert P. Shirtum, Walter L. Wernli, David D. McCoy
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Epoxy resin derived from the highly pure compound and method for preparing the resin and composition
Patent number: 5304624Abstract: 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: GrantFiled: July 9, 1992Date of Patent: April 19, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Naru Koike, Shigeru Iimuro, Mizuo Ito -
Patent number: 5290958Abstract: 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: GrantFiled: August 18, 1993Date of Patent: March 1, 1994Assignee: Industrial Technology Research InstituteInventors: Shyue-Ming Jang, Tian-Shy Shieh
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Patent number: 5278260Abstract: 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: GrantFiled: October 13, 1992Date of Patent: January 11, 1994Assignee: Ciba-Geigy CorporationInventors: Werner Schaffner, Dimiter Hadjistamov
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Patent number: 5245057Abstract: 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: GrantFiled: November 4, 1992Date of Patent: September 14, 1993Assignee: The Dow Chemical CompanyInventor: Robert P. Shirtum
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Patent number: 5242996Abstract: 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: GrantFiled: May 22, 1991Date of Patent: September 7, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
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Patent number: 5239093Abstract: 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: GrantFiled: August 14, 1992Date of Patent: August 24, 1993Assignee: Ciba-Geigy CorporationInventor: Chi-Wen F. Cheng
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Patent number: 5218060Abstract: 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: GrantFiled: February 7, 1992Date of Patent: June 8, 1993Assignee: Ciba-Geigy CorporationInventors: William M. Rolfe, Michael R. Thoseby
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Patent number: 5155202Abstract: 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: GrantFiled: February 6, 1991Date of Patent: October 13, 1992Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hiromi Morita, Kazuyuki Murata, Ichiro Kimura, Susumu Nagao
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Patent number: 5130482Abstract: 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: GrantFiled: December 7, 1990Date of Patent: July 14, 1992Assignee: Daiso Company, Ltd.Inventors: Yoshikazu Takehira, Nobuaki Saragai, Kazuhiro Kitaori
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Patent number: H1439Abstract: 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: GrantFiled: October 18, 1993Date of Patent: May 2, 1995Assignee: The Dow Chemical CompanyInventor: Thomas J. Hairston