Oxirane Ring Is Unsubstituted Or Hydrocarbyl Substituted Only Patents (Class 549/522)
  • Patent number: 10619254
    Abstract: Disclosed herein are methods and systems that relate to various configurations of electrochemical oxidation, chlorine oxidation, oxychlorination, chlorination, and epoxidation reactions to form propylene oxide or ethylene oxide.
    Type: Grant
    Filed: April 26, 2018
    Date of Patent: April 14, 2020
    Assignee: Calera Corporation
    Inventors: Kyle Self, Michael Joseph Weiss, Ryan J Gilliam, Thomas Albrecht, Gal Mariansky
  • Patent number: 9162934
    Abstract: The object of the present invention is to solve the problems in the prior arts, and to find more improved reaction conditions for suppressing the racemization of the product and obtaining an optically active alcohol at a high optical purity. The inventors achieved to solve the above problems by using a solvent system that is capable of resolving both an asymmetric catalyst and a formate salt, allowing the hydrogen source and the asymmetric catalyst to be present in the same phase.
    Type: Grant
    Filed: May 10, 2011
    Date of Patent: October 20, 2015
    Assignee: Kanto Kagaku Kabushiki Kaisha
    Inventors: Taito Hatakeyama, Kunihiko Murata, Kunihiko Tsutsumi, Noriyuki Utsumi
  • Patent number: 8921584
    Abstract: A composition is provided that contains an intermediate for a water-soluble monomer, wherein this intermediate is suitable for producing a water-soluble polyalkylene glycol-type monomer that has a polymerizable terminal double bond, and suitable for the production of water-soluble polymer, and moreover allows the high-yield production of water-soluble polymer. A process of producing this composition and a water-soluble monomer-containing composition obtained therefrom are also provided. A water-soluble monomer is also provided that can be used as a starting material for a water-soluble polymer that even at high hardnesses exhibits an excellent capacity to capture metal ions such as the calcium ion and magnesium ion, an excellent anti-gelation performance, an excellent anti-soil redeposition performance, a better anti-dye transfer performance than in the past, and also an excellent compatibility with surfactants.
    Type: Grant
    Filed: December 3, 2010
    Date of Patent: December 30, 2014
    Assignee: Nippon Shokubai Co, Ltd
    Inventors: Atsuro Yoneda, Makoto Saito, Aki Tsukajima, Daisuke Michitaka, Mitsuaki Makino
  • Publication number: 20130123521
    Abstract: A process for preparing a divinylarene dioxide including (a) reacting at least one divinylarene with hypochlorous acid to form a chlorohydrin; and (b) treating the chlorohydrin formed in step (a) with at least one base, under conditions to form a divinylarene dioxide product.
    Type: Application
    Filed: March 4, 2011
    Publication date: May 16, 2013
    Inventors: Eric B. Ripplinger, David L. Jean, David L. Burow, Khiet T. Pham, Maurice J. Marks, Gyongyi Gulyas
  • Patent number: 8338627
    Abstract: A process for producing epoxide, the process including contacting an organic phase including at least one halohydrin(s) with at least one aqueous phase including a base in a plug-flow mixer/reactor system to disperse the organic phase in the aqueous phase via a mixing device imparting a power-to-mass ratio of at least 0.2 W/kg to convert at least a portion of the at least one halohydrin to an epoxide.
    Type: Grant
    Filed: July 30, 2009
    Date of Patent: December 25, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Ranate Patrascu, Bruce D. Hook, Charles W. Lipp, Michael D. Cloeter, Heinz Groenewald
  • Patent number: 8252959
    Abstract: A process for the preparation of an 1,1-disubstituted oxirane is disclosed, wherein an organic sulphide is reacted in a polar solvent with an educt containing a leaving group attached to a primary or secondary carbon atom, and/or the sulfonium salt formed in this way is reacted with a ketone in presence of a base and a polar solvent. Oxiranes of the type obtained may be further converted into the corresponding ?-hydroxyketone or ?-aminoketone, either in one step by subjecting to aerobic oxidation in the presence of a transition metal catalyst, or in two steps by hydrolyzation in the presence of an aqueous acid to the corresponding dialcohol and subsequent selective oxidation. Further described are some novel epoxide intermediates. The ?-hydroxyketones and ?-aminoketones thus obtainable are useful inter alga as photoinitiators.
    Type: Grant
    Filed: June 29, 2005
    Date of Patent: August 28, 2012
    Assignee: BASF SE
    Inventors: Nicole End, Reinhard H. Sommerlade, Yvonne Richter
  • Publication number: 20120209015
    Abstract: A process for preparing a divinylarene dioxide including reacting (a) at least one divinylarene with (b) at least one oxidant in the presence of (c) at least one transition metal complex catalyst, and (d) optionally, in the presence of a solvent, and (e) optionally in the presence of a catalyst modifier under conditions to form a divinylarene dioxide product.
    Type: Application
    Filed: October 15, 2010
    Publication date: August 16, 2012
    Inventors: Gyongyi Gulyas, Ashwin R. Bharadwaj, Robert J. Wright, Marty J. Null, Eric B. Ripplinger
  • Publication number: 20120004432
    Abstract: The present invention relates to a process for the catalytic halogenation of an organic compound comprising at least one vicinal diol moiety, said process comprising a step of bringing the organic compound comprising at least one vicinal diol moiety into contact with a hydrogen halide in the presence of a catalyst, characterized in that the catalyst is an organic compound comprising a ?-diketone moiety or a ?-keto aldehyde moiety.
    Type: Application
    Filed: March 17, 2010
    Publication date: January 5, 2012
    Applicant: AKZO NOBEL N.V.
    Inventors: Antoon Jacob Berend Ten Kate, Richard Herman Woudenberg, Eilertdina Henderika Renkema, Luc Louis Theophile Vertommen, Carolina Anna Maria Christina Dirix, Tim Baks
  • Patent number: 8039650
    Abstract: A diamine and an epihalohydrin are subjected to ring-opening addition reaction in the presence of water, to thereby produce a tetrahalohydrinamino compound (i.e., halohydrin compound). Thereafter, the halohydrin compound is reacted with an alkali metal hydroxide in the co-presence of a phase-transfer catalyst, to thereby allow cyclization reaction to proceed. An alkali metal halide by-produced during the cyclization reaction is dissolved in water and removed through phase separation. The resultant organic layer is washed with water for phase separation. Then, a crude tetraglycidylamino compound obtained by recovering unreacted epihalohydrin through evaporation is dissolved in an organic solvent and washed with water for phase separation. Subsequently, the organic solvent is recovered through evaporation under reduced pressure with heating, to thereby isolate a tetraglycidylamino compound (i.e., a product of interest).
    Type: Grant
    Filed: May 8, 2008
    Date of Patent: October 18, 2011
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideharu Kurashima, Tsutomu Numoto, Jyunichi Hisae
  • Publication number: 20110166369
    Abstract: Process for purifying hydrogen chloride, comprising at least one step of bringing said hydrogen chloride into contact with a scrubbing agent containing at least one chlorohydrin.
    Type: Application
    Filed: September 11, 2009
    Publication date: July 7, 2011
    Applicant: SOLVAY SA
    Inventors: Philippe Krafft, Patrick Gilbeau
  • Publication number: 20110054196
    Abstract: [Problem] A catalyst that enables to produce ethylene oxide in high efficiency and high selectivity, and a method for the production of ethylene oxide using the catalyst are provided. [Technical Solution] A catalyst for the production of ethylene oxide comprising a catalyst component supported on a carrier comprising ?-alumina as a main component, having a crush strength of at least 40 N, a specific surface area of at least 1.0 m2/g, and a geometrical shape of a hollow cylinder, characterized in that the catalyst is used by packing in a reaction tube with an inner diameter of at least 28 mm, of a reactor for producing ethylene oxide; and a length/outer diameter ratio in the hollow cylinder is from 0.5 to 1.5, and an inner diameter/outer diameter ratio in the hollow cylinder is within a range of from 0.38 to 0.80.is provided.
    Type: Application
    Filed: March 18, 2009
    Publication date: March 3, 2011
    Inventors: Hiroyuki Hirota, Masatsugu Mikawa
  • Patent number: 7786318
    Abstract: Titanium silicallite crystals useful as catalyst for the production of propylene oxide are prepared by forming a solution of a silicon component, a titanium component and a template, the mol ratio of template to silicon component being 0.25 or less and heating the solution to reaction temperature at a rate not to exceed 0.3° C./min.
    Type: Grant
    Filed: April 12, 2005
    Date of Patent: August 31, 2010
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Joseph E. Remias, Edrick Morales
  • Publication number: 20100029960
    Abstract: A process for producing epoxide, the process including contacting an organic phase including at least one halohydrin(s) with at least one aqueous phase including a base in a plug-flow mixer/reactor system to disperse the organic phase in the aqueous phase via a mixing device imparting a power-to-mass ratio of at least 0.2 W/kg to convert at least a portion of the at least one halohydrin to an epoxide.
    Type: Application
    Filed: July 30, 2009
    Publication date: February 4, 2010
    Applicant: THE DOW CHEMICAL COMPANY
    Inventors: William W. Fan, Christian D. Kneupper, Sascha N. Noormann, Renate P. Patrascu, Bruce D. Hook, Charles W. Lipp, Michael D. Cloeter, Heinz G. Groenewald
  • Patent number: 6888012
    Abstract: A process of preparing an optically active halohydrin compound characterized by comprising asymmetric hydrogen transfer reduction of an ?-haloketone compound in the presence of a group 9 transition metal compound having a substituted or unsubstituted cyclopentadienyl group and an optically active diamine compound. The asymmetric hydrogen transfer reduction is preferably conducted in the presence of a base.
    Type: Grant
    Filed: December 18, 2001
    Date of Patent: May 3, 2005
    Assignee: Ajinomoto Co., Inc.
    Inventors: Takayoshi Torii, Takayuki Hamada, Tomoyuki Onishi, Kunisuke Izawa, Takao Ikariya, Ryoji Noyori
  • Patent number: 6713589
    Abstract: This invention provides a compound suitable as an encapsulating material for electronic devices and having a high Tg, low moisture-absorption, high adhesion and fluidity which is a cyclopentylene compound represented by Formula (I) and its intermediate cyclopentenyl compound represented by Formula (III). In the formula, m is 0 or more, Ar1 and Ar2 are each a phenol residual group, a naphthol residual group or a fluorene derivative residual group, and each contain a hydroxyl group or a glycidyloxyl group.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: March 30, 2004
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Fumio Furusawa, Seiichi Akagi, Akihiro Kobayashi, Hideki Yokoyama
  • Patent number: 6613849
    Abstract: The terminal glydidyl groups of a diglycidyl ether of a hydroxyaliphatic bisphenol is optionally reacted with (meth)acrylic acid to obtain a vinyl ester. The internal hydroxyaliphatic groups are reacted with (meth)acrylic acid or cyanoacrylic acid to prepare a diglycidyl and/or (meth)acrylate-terminated (meth)acrylate or urethane acrylate.
    Type: Grant
    Filed: November 16, 2001
    Date of Patent: September 2, 2003
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Robert E. Hefner, Jr., Katherine S. Clement
  • Patent number: 6576690
    Abstract: The present invention relates to a phosphorous-containing flame retarding epoxy resin and their composition comprising the nitrogen-containing flame retarding epoxy resin. More specifically, the present invention relates to a flame retarding epoxy resin having a pendent phosphorous-containing functional group and their composition comprising the nitrogen-containing flame retarding epoxy resin. The flame retarding phosphorous-containing epoxy resin and the epoxy resin composition containing the same of the present invention possess excellent flame retarding property and heat resistance without containing halogen and diantimony trioxide. Therefore they are useful as an encapsulating material in the semiconductor industry and the cured article prepared from the composition exhibits excellent molding ability and excellent reliance.
    Type: Grant
    Filed: March 22, 2002
    Date of Patent: June 10, 2003
    Assignee: Chang Chung Plastics Co., Ltd.
    Inventors: Kuen-Yuan Hwang, Hong-Hsing Chen, Chih-Fu Chen
  • 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: 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: 6353079
    Abstract: The present invention concerns hydroxyaliphatic functional diglycidyl ethers of bisphenols (epoxy resins); curable (thermosettable) mixtures of at least one hydroxyaliphatic functional epoxy resin and at least one curing agent and/or catalyst therefor, as well as cured (thermoset) compositions prepared therefrom; and derivatives prepared therefrom. The bisphenol precursor to the diglycidyl ether contains a hydroxyaliphatic group linkage between the two aromatic rings of the bisphenol.
    Type: Grant
    Filed: July 26, 2000
    Date of Patent: March 5, 2002
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Robert E. Hefner, Jr., Katherine S. Clement
  • Patent number: 6329492
    Abstract: This invention provides a compound suitable as an encapsulating material for electronic devices and having a high Tg, low moisture-absorptive, high adhesion and rich fluidity, which is a cyclopentylene compound represented by Formula (I) and its intermediate cyclopentenyl compound represented by Formula (III). In the formula, m is 0 or more, Ar1 and Ar2 are each a phenol residual group, a naphthol residual group or a fluorene derivative residual group, and each contain a hydroxyl group or a glycidyloxyl group.
    Type: Grant
    Filed: August 13, 1999
    Date of Patent: December 11, 2001
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Fumio Furusawa, Seiichi Akagi, Akihiro Kobayashi, Hideki Yokoyama
  • Patent number: 5717116
    Abstract: The present invention provides a process for producing (R)-styrene oxides represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and X are as defined in the specification, which comprises treating a mixture of (R)- and (S)-phenylhalogenomethylcarbinols with a lipase in the presence of a carboxylate to preferentially convert the (S)-phenylhalogenomethylcarbinols, and treating a mixture of the formed carbinol alkylates (3) and (R)-phenylhalogenomethylcarbinols with a base to cyclize the (R)-phenylhalogenomethylcarbinols, and also provides an industrially excellent process for producing (R)-styrene oxides (1) which comprises using a mixture enriched with (R)-phenylhalogenomethylcarbinols as the mixture of (R)- and (S)-phenylhalogenomethylcarbinols (2).
    Type: Grant
    Filed: March 29, 1996
    Date of Patent: February 10, 1998
    Assignee: Sumika Fine Chemicals Company, Limited
    Inventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 5532389
    Abstract: A process of preparing alkylene oxides comprises steps of: (1) optionally forming a hypochlorite solution; (2) contacting chlorine with a solution of a hypochlorite below about 60.degree. C., and a pH of less than about 5.5, with sufficient micromixing to achieve a product hypochlorous acid in a yield of at least about 80 percent; (3) separating at least a portion the hypochlorous acid from an aqueous metal chloride solution wherein the solution is sprayed as droplets; (4) distilling the remaining liquid phase; (5) absorbing the hypochlorous acid and dichlorine monoxide in low-chlorides water to produce a low-chlorides aqueous hypochlorous acid solution; (6) contacting the low-chlorides aqueous hypochlorous acid solution with an olefin in a continuous process to form a olefin chlorohydrin; (7) optionally contacting the olefin chlorohydrin with a base to form a alkylene oxide and a salt solution; and (8) optionally separating the alkylene oxide from the salt solution.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: July 2, 1996
    Assignee: The Dow Chemical Company
    Inventors: David L. Trent, George J. Quarderer, Kim G. Bargeron, Douglas C. Greminger, David J. Koranek, Erik J. Stewart, Curtis N. Swisher, Cheryl A. Tirtowidjojo, Danil Tirtowidjojo
  • Patent number: 5523425
    Abstract: In a process for producing a chlorohydrin an olefinically unsaturated compound is reacted with chlorine in the presence of water. Water is applied as a film on a solid support in a reaction zone and/or water droplets are dispersed in the reaction zone. The reaction is conducted at a pressure of up to about 10 bar.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: June 4, 1996
    Assignee: The Dow Chemical Company
    Inventors: Gunther A. Pech, Werner J. Witzl
  • Patent number: 5486627
    Abstract: Described herein is a method for producing epoxides which is continuous, inhibits formation of chlorinated byproducts, and eliminates or substantially reduces waste water discharge. The method includes:(a) forming a low chlorides aqueous hypochlorous acid solution;(b) contacting the low chlorides aqueous hypochlorous acid solution with at least one unsaturated organic compound to form an aqueous organic product comprising at least olefin chlorohydrin;(c) contacting at least the olefin chlorohydrin with an aqueous alkali metal hydroxide to form an aqueous salt solution product containing at least epoxide; and(d) isolating the epoxide from the aqueous salt solution;wherein water is recovered from the product of at least Step (b) and recycled into Step (a) for use in forming the low chlorides aqueous hypochlorous acid solution.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: January 23, 1996
    Assignee: The Dow Chemical Company
    Inventors: George J. Quarderer, Jr., Curtis N. Swisher, David L. Trent
  • Patent number: 5453204
    Abstract: Production of propylene oxide by hydrolysis of propylene chlorohydrin in an aqueous alkaline reaction medium having a pH above 12 and a temperature of at least about 85.degree. C., is conducted in the presence of a small scale-inhibiting amount of a scale inhibitor added as a water-soluble polymer of acrylic acid having a weight average molecular weight in the range of about 1000 to about 5000, and in the absence of any phosphorus-containing additive component. A significant increase in acrylic polymer performance occurs under these high pH conditions as compared to performance at lower pH. Moreover, experiments have shown that no scale deposits were formed in a hydrolyzer unit operated for 180 days under conditions which normally require removal of deposits after 90 days of operation.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: September 26, 1995
    Inventor: John R. Alberty
  • Patent number: 5428180
    Abstract: A method is provided for oxidizing alkenes to epoxides by treating the alkene with a transition metal ion complex which includes a salen or salophen derivative and peroxymonosulfate ion or hypochlorite ion in a two phase system with a phase transfer catalyst, a water phase having a pH from about 6 to about 12.9 and an inorganic solvent phase in which the complex is sufficiently soluble.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: June 27, 1995
    Assignee: The Research Foundation of State University of New York
    Inventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
  • 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: 5126464
    Abstract: A 13 or 14 member macrocyclic compound having the following ring nucleus: ##STR1## wherein: n=0 or 1;m=0 or 1;n+m>0;X.sub.1, X.sub.2, Z.sub.1 and Z.sub.2 independently represent H.sub.2 or O;Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 independently represent H, lower alkyl or CH.sub.2 COOH;L.sub.1 and L.sub.2 independently represent side chains of alpha amino acids, except that L.sub.1 and L.sub.2 do not both represent H; andR.sub.1 and R.sub.2 independently represent H or OH forms stable complexes with transition metal ions that may be used as catalysts for oxidizing alkenes to epoxides with oxidizing agents.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: June 30, 1992
    Assignee: The Research Foundation of State University of New York
    Inventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
  • Patent number: 4980485
    Abstract: Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: December 25, 1990
    Assignee: Japan Tobacco Inc.
    Inventors: Kenji Mori, Takeshi Kitahara, Koshi Koseki
  • Patent number: 4933477
    Abstract: Phenyl-substituted epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, alkyl, alkenyl, phenyl, halogen, nitro, alkoxy, haloalkyl, phenoxy or phenylsulfonyl, are prepared by reducing a haloacetophenone to a halohydrin and reacting the halohydrin with an alkali metal hydroxide by a process in which the reduction with the alkali metal borohydride and the reaction are carried out in aqueous organic solution, or the cyclization of a halohydrin with an alkali metal hydroxide is carried out in an organic liquid.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: June 12, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Hans-Gert Recker, Hubert Smuda
  • Patent number: 4916202
    Abstract: The present invention provides an epoxy resin of the formula ##STR1## where A is selected from the group consisting of --C(CH.sub.3).sub.2 --, --C(CF.sub.3).sub.2 --, --S--, --SO.sub.2 --, --CH.sub.2 --, --CO--, --O--, and --C.sub.3 H.sub.6 --, and each B.sub.1, B.sub.2, B.sub.3, and B.sub.4 is independently selected from the group consisting of --H, --F, --Cl, --Br, --I, --CH.sub.2 CH.dbd.CH.sub.2, --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, and --C.sub.4 H.sub.9.The present invention also provides a curable composition comprising an epoxy resin of the foregoing formula (I) and an effective curing amount of a hardener for an epoxy resin. The moisture sensitivity of the cured castings and/or composites based on the epoxy resins is lower than known epoxy resin castings and/or composites that have comparable thermal stability, modulus, strength, processability, and toughness.
    Type: Grant
    Filed: September 17, 1987
    Date of Patent: April 10, 1990
    Assignee: University of Dayton
    Inventors: John M. Butler, Richard P. Chartoff, James A. Harvey
  • Patent number: 4680341
    Abstract: Novel 3-ring tetraglycidates having the formula ##STR1## wherein X=O, S, ##STR2## --CH.sub.2 --, C.dbd.O; Y=halogen, C.sub.1 -C.sub.4 alkyl; and p0 n=0 to 4, are disclosedEpoxy resin systems exhibiting good tensile properties and moisture sensitivity can be made by copolymerizing the tetraglycidates with a polyamine curing agent. Prepregs can be made by combining the epoxy resin systems with a fiber reinforcement. The epoxy resin system may include a co-epoxide.
    Type: Grant
    Filed: April 17, 1986
    Date of Patent: July 14, 1987
    Assignee: Union Carbide Corporation
    Inventor: Richard H. Newman-Evans
  • Patent number: 4496752
    Abstract: Chlorine and tertiary alkanol dissolved in an inert organic solvent are reacted with aqueous alkali to produce tertiary alkyl hypochlorite which is recovered in the organic solvent and reacted with water and olefinically unsaturated compound to produce chlorohydrin and tertiary alkanol. Chlorohydrin and tertiary alkanol recovered in the organic solvent are contacted with aqueous alkali to produce the epoxy compound, and tertiary alkanol recovered in the organic solvent is recycled to hypochlorite production. The process may be integrated with the electrolytic production of chlorine, with an appropriate treatment of the recycle aqueous stream when required.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: January 29, 1985
    Assignee: The Lummus Company
    Inventors: Abraham P. Gelbein, Joon T. Kwon
  • Patent number: 4496753
    Abstract: A chlorohydrin, such as glycerol dichlorohydrin is saponified in two stages, with the first stage being carried out in a high back-mix saponification reactor, and the second stage being carried out in a plug-flow saponification reactor. The use of two different stages improves both selectivity and yield.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: January 29, 1985
    Assignee: Lummus Crest, Inc.
    Inventors: Joon T. Kwon, George D. Suciu
  • Patent number: 4443620
    Abstract: Chlorine and tertiary alkanol dissolved in an inert organic solvent are reacted with calcium oxide in aqueous calcium chloride to produce tertiary alkyl hypochlorite which is recovered in the organic solvent and reacted with water and olefinically unsaturated compound to produce chlorohydrin and tertiary alkanol. Chlorohydrin and tertiary alkanol recovered in the organic solvent are contacted with calcium oxide in aqueous calcium chloride to produce the epoxy compound, and tertiary alkanol recovered in the organic solvent is recycled to hypochlorite production. Calcium chloride produced as by-product in the hypochlorite production and saponification is recovered as an aqueous solution having a calcium chloride concentration of at least 25 wt. % to provide calcium chloride in a usable form.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: April 17, 1984
    Assignee: The Lummus Company
    Inventors: Abraham P. Gelbein, Arthur S. Nislick
  • Patent number: 4410714
    Abstract: A process for producing an epoxy compound by chlorinating a tertiary alkanol to the corresponding hypochlorite, followed by reaction of the hypochlorite with water and an olefinically unsaturated compound to produce the corresponding chlorohydrin and saponification of the chlorohydrin to the corresponding epoxy compound. The hypochlorite production and the saponification are effected with calcium oxide in an aqueous solution of calcium chloride, with calcium chloride being produced as by-product in an aqueous solution having a calcium chloride concentration of at least 25 wt. %. In this manner, calcium chloride by-product is recovered in a more usable form thereby eliminating the problems associated with recovery of calcium chloride by-product.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: October 18, 1983
    Assignee: The Lummus Company
    Inventor: George J. Apanel
  • Patent number: 4376865
    Abstract: Olefin is reacted with alkyl hypochlorite and water to produce an effluent containing the chlorohydrin and alkanol. An organic solvent is employed to extract the alkanol and chlorohydrin from the aqueous effluent, followed by saponification with base to produce olefin oxide. Olefin oxide is separated from the saponification effluent, followed by separation of an organic phase of the organic solvent, and an aqueous phase, which contains the alkanol. The aqueous phase containing alkanol, is chlorinated to produce the alkyl hypochlorite, with the organic phase being recycled to the extraction. The process is preferably integrated with the electrolytic production of chlorine.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: March 15, 1983
    Assignee: The Lummus Company
    Inventor: George J. Apanel