Glycidyl Ether Formed By Bonding Oxygen Directly To An Acyclic Carbon Which Is Bonded Directly To An Oxirane Ring Patents (Class 549/516)
  • Patent number: 9394265
    Abstract: A production method by which an alkyldiol monoglycidyl ether can be efficiently produced without requiring a complex purification step is provided. A method for producing an alkyldiol monoglycidyl ether, including a step of reacting a vinyl ether-containing alcohol with an epihalohydrin to form a vinyl ether-containing glycidyl ether, conducting a devinylation reaction in the presence of an acid catalyst and water, and further conducting an acetal decomposition reaction by adding an acid aqueous solution.
    Type: Grant
    Filed: July 17, 2012
    Date of Patent: July 19, 2016
    Assignee: HITACHI CHEMICAL COMPANY, LTD.
    Inventor: Junichi Kamei
  • Publication number: 20150094478
    Abstract: Provided is a production method which is capable of efficiently producing an alkanediol glycidyl ether (meth)acrylate with high purity and high yield without requiring a troublesome purification process. A method for producing an alkanediol glycidyl ether (meth)acrylate, which comprises: a step wherein a vinyloxyalkyl glycidyl ether is subjected to a devinylation reaction in the presence of an acid catalyst and water; and a subsequent step wherein an esterification reaction is carried out.
    Type: Application
    Filed: April 25, 2013
    Publication date: April 2, 2015
    Inventor: Junichi Kamei
  • Patent number: 8981127
    Abstract: The present invention relates to a process for the preparation of nebivolol and, more particularly, to an improved process of synthesizing an alpha-haloketone of formula a key intermediate in the preparation of nebivolol.
    Type: Grant
    Filed: September 22, 2009
    Date of Patent: March 17, 2015
    Assignee: Zach System
    Inventors: Yvon Derrien, Eric Chenard, Alain Burgos
  • Publication number: 20140163246
    Abstract: A production method by which an alkyldiol monoglycidyl ether can be efficiently produced without requiring a complex purification step is provided. A method for producing an alkyldiol monoglycidyl ether, including a step of reacting a vinyl ether-containing alcohol with an epihalohydrin to form a vinyl ether-containing glycidyl ether, conducting a devinylation reaction in the presence of an acid catalyst and water, and further conducting an acetal decomposition reaction by adding an acid aqueous solution.
    Type: Application
    Filed: July 17, 2012
    Publication date: June 12, 2014
    Inventor: Junichi Kamei
  • Patent number: 8697902
    Abstract: A process for the hydrocyanation of a hydrocarbon-based compound having at least one site of ethylenic unsaturation into a nitrile compound includes reaction thereof, in a liquid medium, with hydrogen cyanide in the presence of a catalyst containing a metal element selected from among the transition metals and an organophosphorus ligand, wherein the organophosphorus ligand is a compound of formula (I): The subject process is particularly useful for the synthesis of adiponitrile from butadiene.
    Type: Grant
    Filed: June 5, 2009
    Date of Patent: April 15, 2014
    Assignee: Rhodia Operations
    Inventor: Sergio Mastroianni
  • Patent number: 8399692
    Abstract: Product containing epichlorohydrin, wherein the amount of trichloropropane is of less than 0.01 g of trichloropropane per kg of product, a process for manufacturing the product and its use in various applications.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: March 19, 2013
    Assignee: Solvay (Societe Anonyme)
    Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Noel Boulos
  • Patent number: 8378130
    Abstract: Product containing epichlorohydrin and at least one alkyl glycidyl ether in an amount of less than 0.1 g/kg of product. Use of the product containing epichlorohydrin in the manufacture of epoxy resins, of glycidyl ethers, of glycidyl esters, of glycidyl amides, of glycidyl imides, of products that will be used in food and drink applications, of cationization agents, and of flame retardants, of products which will be used as detergent ingredient and of epichlorohydrin oligomers.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: February 19, 2013
    Assignee: SOLVAY (Societe Anonyme)
    Inventors: Noel Boulos, Philippe Krafft, Patrick Gilbeau, Dominique Balthasart
  • Publication number: 20120245301
    Abstract: Disclosed is a method for activating a solid support material with epoxy groups and for immobilising ligands thereon, utilising phase transfer catalytic conditions. The method permits the introduction of epoxy groups and specific nucleophilic ligands on the support material with a high level of substitution. Furthermore, the invention provides a general method for immobilising a ligand for use in a wide variety of chromatographic separation procedures such as ion exchange chromatography, hydrophobic interaction chromatography (HIC), reverse phase chromatography (RPC), or affinity chromatography.
    Type: Application
    Filed: June 6, 2012
    Publication date: September 27, 2012
    Applicant: GE HEALTHCARE BIO-SCIENCES AB
    Inventors: GUNNAR GLAD, JEAN-LUC MALOISEL, NICOLAS THEVENIN
  • Patent number: 8273853
    Abstract: Disclosed is a process for the preparation of emulsifiers E1 which are obtained by (a) reacting a polyol with propylene oxide or a mixture of ethylene oxide and propylene oxide, to give an intermediate Z1, (b) reacting the intermediate Z1 with epichlorohydrin, forming an intermediate Z2, (c) reacting the intermediate Z2 with an adduct of ethylene oxide or a mixture of ethylene oxide and propylene oxide, with a C1-C22 monoalcohol, provided that on average at least one epoxide function of the intermediate Z2 is reacted and on average at least one epoxide function originating from the intermediate Z2 is retained. Compounds E1 are suitable as emulsifiers for preparing aqueous emulsions or dispersions of epoxy resins.
    Type: Grant
    Filed: April 3, 2009
    Date of Patent: September 25, 2012
    Assignee: Cognis IP Management GmbH
    Inventors: Paul Birnbrich, Hans-Josef Thomas, Giorgio Sabbadini, Ulrich Nagorny, Georg Bourscheidt
  • Patent number: 7829639
    Abstract: A composition for conductive materials comprises a compound represented by the following general formula (A1): wherein: R1 is the same or different and each independently represents a C2-C8 straight-chain alkyl group; R2 is the same or different and each independently represents a hydrogen atom, a methyl group or an ethyl group; Y represents a group containing at least one substituted or unsubstituted aromatic hydrocarbon ring, or substituted or unsubstituted heterocyle; and X1 is the same or different and each represents a substituent represented by the following general formula (A2): wherein n1 is an integer of from 2 to 8.
    Type: Grant
    Filed: September 2, 2005
    Date of Patent: November 9, 2010
    Assignee: Seiko Epson Corporation
    Inventors: Koichi Terao, Yuji Shinohara, Takashi Shinohara
  • Patent number: 7468415
    Abstract: It was found that glycidyloxystyrenes, including glycidyloxystyrene and substituted glycidyloxystyrene, can be synthesized from hydroxycinnamic acid or substituted hydroxycinnamic acids in a one-pot, two-step process. The substrate can be thermally decarboxylated and then without purification, reacted in the presence of a halomethyl-oxirane and a base. The resulting product can be polymerized or coppolymerized to a fully substituted product.
    Type: Grant
    Filed: December 20, 2007
    Date of Patent: December 23, 2008
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Keith Kunitsky, Mukesh C. Shah, Steven W. Shuey, Mark E. Wagman
  • Patent number: 7012120
    Abstract: This invention relates to thermosetting resin compositions useful for mounting onto a circuit board semiconductor devices, such as CSPs, BGAs, LGAs and the like, each of which having a semiconductor chip, such as LSI, on a carrier substrate. The compositions of this invention are reworkable when subjected to appropriate conditions.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: March 14, 2006
    Assignee: Henkel Corporation
    Inventors: Philp T. Klemarczyk, Andrew D. Messana, Afranio Torres-Filho, Erin K. Yaeger, Takahisa Doba
  • Patent number: 6982349
    Abstract: The present invention relates to an improved process for producing optically active (S)-atenolol of formula (1) in high optical purity by reacting a phenol with an epichlorohydrin.
    Type: Grant
    Filed: November 5, 2003
    Date of Patent: January 3, 2006
    Assignee: Emcure Pharmaceuticals Limited
    Inventors: Satish Ramanlal Mehta, Baburao Manikroa Bhawal, Vishnu Hari Deshpande, Mukund Keshav Gurjar
  • Patent number: 6399767
    Abstract: A process for preparing a compound having structure (I) wherein n is an integer from 1-5; each of R1 and R2 independently is optionally substituted C1-C6 alkyl; each of W and X is independently hydrogen or C1-C6 alkyl; Y is O, S or NR3 where R3 is hydrogen, C1-C6 alkyl or a protective group; and Z is a CD ring structure, a steroid structure, or a vitamin D structure, each of which optionally having structure (IV) wherein W, X, Y and Z are defined above, in the presence of a base, with a compound having structure (V) or (v′) wherein n, R1 and R2 are as defined above, and E is an eliminating group.
    Type: Grant
    Filed: May 22, 2000
    Date of Patent: June 4, 2002
    Assignees: The Trustees of Columbia University in the City of New York, Chugai Seiyaku Kabushiki Kaisha
    Inventors: David A. Horne, Noboru Kubodera, Hiroshi Suzuki, Hitoshi Shimizu
  • 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
  • Patent number: 6372923
    Abstract: The present invention provides a process for preparing an alcohol derivative, where the alcohol derivative is an ester, acetal, ketal, ether glycoside, or alkyl glycoside, by reacting an alcohol with a carbonyl compound, alcohol, olefin, epoxy compound or saccharide, where C2-4 vicinal alkylene oxides are excluded, in the presence of (A) an aluminum alkoxide and (B) sulfuric acid or phosphoric acid.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: April 16, 2002
    Assignee: Kao Corporation
    Inventors: Mitsuru Uno, Munehisa Okutsu, Tomohito Kitsuki
  • 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: 6288248
    Abstract: Epichlorohydrin-based product containing at least 99.9% by weight of epichlorohydrin and a total amount of chloro impurities of less than or equal to 150 ppm by weight, and process for manufacturing this product by reaction of allyl chloride with a peroxide compound in the presence of water, a catalyst and a diluent in at least one reactor, and separation of the epichlorohydrin formed.
    Type: Grant
    Filed: November 25, 1998
    Date of Patent: September 11, 2001
    Assignee: Solvay (Société Anonyme)
    Inventors: Michel Strebelle, Patrick Gilbeau, Jean-Pierre Catinat
  • 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: 6218430
    Abstract: The present invention relates to non-secosteroidal compounds which activate and modulate the vitamin D receptor (VDR). Because compounds of the present invention display many of the beneficial properties of 1,25(OH)2D3, but with reduced calcium mobilization effects, they may be used advantageously to treat and prevent conditions that show vitamin D sensitivity. Such disease states typically show abnormal calcium regulatory, abnormal immune responsive, hyperproliferative, and/or neurodegenerative characteristics.
    Type: Grant
    Filed: August 24, 1998
    Date of Patent: April 17, 2001
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Elizabeth A. Allegretto, Marcus F. Boehm, Alex M. Nadzan
  • Patent number: 6207845
    Abstract: An aluminum compounds represented by the following general formula (1): Al(R1—SO3)1(R2)m(R3)n   (1) wherein R1 is a hydrocarbon group which may be substituted, R2 is a hydrocarbon group which may be substituted, an aliphatic hydrocarbonoxy group which may be substituted, or a halogen atom, R3 is an aromatic hydrocarbonoxy group which may be substituted, and 1, m and n are independently a number of 0 to 3, with the proviso that 1+m+n equals 3, and 1 is not 0, an acid catalyst comprising the aluminum compound, and a process for producing an ester, acetal, ketal, ether or alkyl glycoside making use of the catalyst. The catalyst is suitable for use in a variety of acid-catalyzed reactions of alcohols, i.e., reactions with carbonyl compounds, such as esterification, transesterification, acetalization and ketalization, etherification, ring-opening reactions of epoxy compounds, etc.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: March 27, 2001
    Assignee: Kao Corporation
    Inventors: Munehisa Okutsu, Tomohito Kitsuki, Katsumi Kita
  • 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: 5728796
    Abstract: A process reaction between: (1) a compound that contains one or more epoxide moieties per molecule, and (2) a compound that contains one or more primary aliphatic hydroxyl groups per molecule; is catalyzed by: (3) a catalyst compound containing one or more trifluoromethanesulfonate moieties and one or more silyl moieties and run at a temperature of no more than 130.degree. C., such that the catalyst preferably catalyzes reaction at the primary aliphatic hydroxyl group, so that the resulting resin does not gel.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: March 17, 1998
    Assignee: The Dow Chemical Company
    Inventors: Zeng K. Liao, James L. Bertram
  • Patent number: 5616800
    Abstract: This invention relates to novel dicationic and polycationic monoprimary alcohol compounds and their derivatives, represented by the formula ##STR1## wherein each alk is independently alkyl of 1-8 carbon atoms; each ALK is independently alkyl of 1-8 carbon atoms; each R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 is independently H or alkyl of 1-8 carbon atoms; n is 2-5; G is H, CR.sub.1 R.sub.2 CR.sub.3 OHCR.sub.4 R.sub.5 X or ##STR2## X is Cl, Br or I; An.sup.- is an anion and p is 1-10; provided that the compound is soluble in water.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: April 1, 1997
    Assignee: The Dow Chemical Company
    Inventors: Dorothy L. Roerden, R. Keith Frank
  • Patent number: 5420312
    Abstract: A process for the production of glycidyl ether of an aliphatic, cycloaliphatic or araliphatic primary or secondary alcohol, comprising:A) reacting epichlorohydrin with a molar excess of the alcohol in the presence of a Lewis acid catalyst; optionallyB) dehydrochlorinating the product so obtained; andC) reacting the product from step A) or B) with a molar excess of epichlorohydrin in the presence of alkali and a phase transfer catalyst, and then isolating the glycidyl ether product so obtained.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: May 30, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Christopher M. Andrews, Bryan Dobinson, William M. Rolfe, Michael R. Thoseby
  • Patent number: 5342903
    Abstract: A process for the preparation of adducts by reacting an alcohol with an epoxy compound in the presence of a catalyst, which comprises reacting an alcohol of formula I ##STR1## wherein A is an aliphatic, cycloaliphatic or araliphatic radical and r is a number from 1 to 10, with a mono- or diepoxide in the equivalent ratio of 1:20 to 20:1, based on the hydroxyl and epoxy groups, in the presence of a metal complex of formula II as catalyst[M.sup.n+ (L.sub.1).sub.x (L.sub.2).sub.y (L.sub.3.sup.m-).sub.z ][X.sup.k- ].sub.(n-zm)/k (II),whereinM is a metal of the main groups or subgroups of the Periodic Table of the Elements,L.sub.1 and L.sub.2 are weakly bonded, neutral, unidentale or multidentate ligands,L.sub.3 is a strongly bonded, non-replaceable neutral or anionic unidentale or multidentate ligand,X is an anion of the following formulae BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, ClO.sub.4.sup.-, IO.sub.4.sup.-, NO.sub.3.sup.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: August 30, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
  • Patent number: 5245048
    Abstract: A process for the production of a glycidyl ether of an alcohol, comprising reacting an alcohol with epichlorohydrin, in substantially the stoichiometric proportions required to produce the 1:1 adduct, in the presence, as catalyst, of a salt of perchloric acid or trifluoromethane sulphonic acid with a metal of Group IIIA of the Periodic Table of Elements (according to the IUPAC 1970 convention); and then dehydrochlorinating the product so obtained.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: William M. Rolfe, Michael R. Thoseby
  • 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: 5227502
    Abstract: Novel fluorinated unsaturated glycidyl ethers are prepared by reacting 1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol or 1,1,1-trifluoro-2-trifluoromethyl-4-propen-2-ol with chloromethyloxirane in the presence of onium salts. The fluorinated unsaturated glycidyl ethers are, in turn, subject to addition reaction with hydrosilanes in the presence of transition metal catalysts, obtaining novel silicon-modified glycidyl ethers or fluorinated organic silicon compounds.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: July 13, 1993
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Takago, Hiroshi Inomata, Yasuo Tarumi, Hiromasa Yamaguchi, Kenichi Fukuda
  • Patent number: 5162547
    Abstract: An improved process for the preparation of glycidyl ethers of formula I ##STR1## wherein Q is an aliphatic, cycloaliphatic or araliphatic radical of a valency m, R is --H or --CH.sub.3, and m is an integer from 1 to 10,by reacting an alcohol of formula Q--(OH).sub.m with m mol of an epihalohydrin of formula II ##STR2## in the presence of a catalyst to the corresponding halohydrin ether, and dehydrohalogenating said halohydrin ether with an alkali metal hydroxide to give a compound of formula I, wherein Q, m and R are as defined above and Hal is halogen,which process comprises using as catalysta) tin difluoride orb) a divalent tin halide in conjunction with a co-catalyst.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: November 10, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Roth, Heinz Wolleb, Marc-Andre Truffer
  • Patent number: 5128491
    Abstract: The present invention relates to a process for the preparation of a glycidyl ether of a di-secondary alcohol with a monomer content of about 80% to about 90% of the formula (I) ##STR1## comprising the steps of: (a) reacting a di-secondary alcohol of the formula (II) ##STR2## with epichlorohydrin in the presence of an alkali and a phase transfer catalyst to produce a glycidyl ether with a monomer content of about 60% to about 75%; and(b) reacting said glycidyl ether with a monomer content of about 60% to about 75% with epichlorohydrin in the presence of an alkali and benzyltrimethylammonium chloride to produce a glycidyl ether of a di-secondary alcohol with a monomer content of about 80% to about 90%.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: July 7, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Chi-Wen F. Cheng
  • Patent number: 5117010
    Abstract: The present invention relates to the preparation of di-secondary alcohols comprising the reaction of an alcohol and a diglycidyl ether of a dihydric phenol in the presence of a catalyst of the formula (IV):MX (IV)wherein M is a metal from Groups IB to VIIIB or a metal or metalloid from Groups IIA to VA of the Periodic Chart of Elements or an ammonium ion and X is an anion selected from the group consisting of BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, AlF.sub.4.sup.-, TiF.sub.6.sup.2-, SiF.sub.6.sup.2-, and ZrF.sub.6.sup.2- to produce the di-secondary alcohol, which can then be subjected to glycidylation to produce a glycidyl ether, orthe reaction of an alcohol, glycol or polyol and epichlorohydrin in the presence of the foregoing catalyst, followed by ring closure employing an alkali to produce a mono- or polyglycidyl ether. The monoglycidyl ether can be further reacted with a dihydric phenol to produce a di-secondary alcohol which is then glycidylized to produce a glycidyl ether.
    Type: Grant
    Filed: August 15, 1991
    Date of Patent: May 26, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Chi-Wen F. Cheng
  • Patent number: 4924013
    Abstract: A process for the reduction of free epichlorohydrin in epoxy compounds which involves the treatment of an epoxy compound with an alkali metal sulfite, preferably sodium sulfite.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: May 8, 1990
    Assignee: Hi-Tek Polymers, Inc.
    Inventor: Joe M. Hunter
  • Patent number: 4810808
    Abstract: A process for preparing a polyglycidyl compound in which an aromatic hydroxycarboxylic acid having phenolic hydroxyl group is reacted with an epihalohydrin in the presence of a phase transfer catalyst and the dehydrohalogenation is then conducted by acting an aqueous alkali solution on the reaction mixture obtained in the first step.
    Type: Grant
    Filed: July 27, 1987
    Date of Patent: March 7, 1989
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Haruo Tomita, Kazuya Yonezawa
  • Patent number: 4778863
    Abstract: Glycidyl derivatives of compounds containing --OH, --NH.sub.2 and/or --COOH groups are prepared by reacting in the presence of a mixture of solvents, at least one of which is a polar aprotic solvent, an excess of an epihalohydrin with a compound containing --OH, --NH.sub.2 and/or --COOH groups while continuously or incrementally adding an alkali metal hydroxide to the mixture and removing water from the reaction by codistillation with epihalohydrin and the solvents.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: October 18, 1988
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Zeng-kun Liao
  • Patent number: 4661644
    Abstract: Novel ring-brominated derivatives of the diepoxides of tetraalkyl dihydroxydiaromatic compounds, e.g., the diglycidyl ether of 3,5-dibromo-4-(2-(2-bromo-4-hydroxy-3,5-dimethylphenyl)ethyl)-2,6-dimethyl phenol.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: April 28, 1987
    Assignee: The Dow Chemical Company
    Inventors: Harry C. Silvis, Abel Mendoza
  • Patent number: 4624975
    Abstract: The hydrolyzable halide content of glycidyl ethers prepared by dehydrohalogenating a halohydrin ether intermediate product in the presence of an organic solvent, washing the resultant product with water and distilling the solvent from the organic phase from the water wash step is stabilized when the distillation step is conducted in the presence of a sulfonic acid, sulfonic acid ester, organic sulfate or any combination thereof such as p-toluene sulfonate.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: November 25, 1986
    Assignee: The Dow Chemical Company
    Inventor: Ha Q. Pham
  • Patent number: 4623701
    Abstract: Multifunctional epoxy resins are prepared by reacting (1) a polyglycidyl ether of a polyhydroxyl-containing material said glycidyl ether having an average of at least 0.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: November 18, 1986
    Assignee: The Dow Chemical Company
    Inventor: John L. Massingill
  • Patent number: 4474944
    Abstract: An epoxidized polyether, characterized by containing oxytetramethylene units and having in one molecule 0.9 or more epoxy groups on the average represented by the general formula (I): ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are hydrogen atoms or alkyl groups. An epoxy resin obtained from said epoxidized polyether alone or in admixture with an ordinary epoxy compound has a high flexibility.
    Type: Grant
    Filed: April 7, 1983
    Date of Patent: October 2, 1984
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Kenji Yasuda, Yasuaki Yokoyama, Shuichi Matsumoto, Kunihiro Harada
  • Patent number: 4465815
    Abstract: A novel polyhydroxy oligomer crosslinkable with amine-aldehyde to form a coating composition adapted for use as an automotive topcoat which upon curing forms a hard, glossy, durable coating with outstanding weatherability and excellent resistance to solvents and water. The coating composition comprises:(A) a polyhydroxy oligomer having a number average (M.sub.n) molecular weight of between about 300-2000 and being the reaction product of:(i) an acid ester made by reacting(a) a C.sub.3 -C.sub.10 aliphatic branched diol, and(b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio of greater than 1:1 up to 1:2; and(ii) a monoepoxide C.sub.2 -C.sub.10 monomer, the monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide groups for each acid group of the acid ester;(B) an amine-aldehyde crosslinking agent; and(C) optionally a hydroxy functional additive.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: August 14, 1984
    Assignee: Ford Motor Company
    Inventor: Mohinder S. Chattha