Organic Peracid Utilized Patents (Class 549/525)
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Patent number: 6107433Abstract: A vegetable oil-based polyol is made by adding a peroxyacid to vegetable oil wherein said peroxyacid reacts with said vegetable oil to form epoxidized vegetable oil and adding said epoxidized vegetable oil to a mixture of an alcohol, water, and a catalytic amount of fluoboric acid so as to form a vegetable oil-based polyol. A further embodiment of the present invention involves making a vegetable oil-based polyol using an epoxidized vegetable oil as the starting material. The epoxidized vegetable oil undergoes hydroxylation by the same process as outlined above. According to another aspect of the present invention, the vegetable oil-based polyol formed by the novel methods of this invention may be reacted with an isocyanate to form a polyurethane. Alternatively, a filler such as silica may be combined with the vegetable oil-based polyol before it is reacted with the isocyanate. These polyurethanes made from vegetable oil-based polyols may be used to form electroinsulating casting resins.Type: GrantFiled: November 6, 1998Date of Patent: August 22, 2000Assignee: Pittsburg State UniversityInventors: Zoran Petrovic, Andrew Guo, Ivan Javni
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Patent number: 6080894Abstract: The propylene oxide and styrene co-production process generates a heavy residue byproduct containing metals, mainly sodium, which previously was adequate for use only as low quality fuel. According to the invention, the heavy residue is dehydrated in the presence of a strong inorganic acid at temperatures of 150-250.degree. C. and pressures below the atmospheric pressure to yield styrene and recover 2-phenylethanol, a compound used in the perfume industry, and a heavy residue substantially free of metals that may be used as fuel.Type: GrantFiled: March 17, 1998Date of Patent: June 27, 2000Assignee: Repsol Quimica S.A.Inventors: Juan Antonio Delgado Oyague, Pilar De Frutos Escrig, Ignacio Vic Fernandez
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Patent number: 6066751Abstract: It has been surprisingly discovered that the disadvantages of the lengthy literature procedures to synthesize 13,14-dihydro prostaglandin A, E, and F derivatives can be overcome using a novel Methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2 tetramethyl-1-silapropoxy)cyclopentyl) heptanoate intermediate, which can be synthesized from commercially available Methyl 7-[3-(R)-hydroxy-5-oxo-1-cyclopent-1-yl] heptanoate. This novel intermediate can be coupled with oxygen, carbon, sulfur, and nitrogen nucleophiles, in the presence of a base or a Lewis acid, in a ring-opening process to provide 13,14-dihydro prostaglandin A, E, and F derivatives.Type: GrantFiled: September 4, 1998Date of Patent: May 23, 2000Assignee: The Procter & Gamble CompanyInventors: John August Wos, Jack Snyder Amburgey, Jr., Mitchell Anthony deLong, Yili Wang, Haiyan George Dai, Biswanath De
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Patent number: 6063943Abstract: The present invention relates to a heterogeneous polyimide-supported transition metal complex catalyst for epoxidation of olefin, which is prepared by impregnating a heat- and acid-resistant polyimide resin with a homogeneous metal catalyst of molybdenum, vanadium, tungsten or titanium, and a process for preparing epoxy compounds using the same. The heterogeneous polyimide-supported transition metal complex catalyst of the invention provides superior catalytic activity, selectivity and stability in the epoxidation of higher olefin. Further, the catalyst of the invention has strong resistance against heat and acid. Besides, the catalyst of the invention may provide the following advantages which are critical in industrial use: it permits relatively high yield of epoxy compounds; and, it can be easily separated from the reaction product, which eases recycling of the catalyst.Type: GrantFiled: December 11, 1998Date of Patent: May 16, 2000Assignee: Korea Advanced Institute of Science and TechnologyInventors: Son Ki Ihm, Chang Gun Oh, Jou Hyeon Ahn, Jong Chan Kim, David C. Sherrington
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Patent number: 6008386Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.Type: GrantFiled: July 22, 1997Date of Patent: December 28, 1999Assignee: Board of Regents University of Nebraska-LincolnInventors: David B. Berkowitz, Michelle L. Pedersen
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Patent number: 5808114Abstract: Preparation of epoxides from olefins by means of aromatic peroxycarboxylic acids comprises a step A of epoxidizing the olefin and removing the resulting aromatic carboxylic acid from the epoxide, a step B of catalytically hydrogenating the removed aromatic carboxylic acid to the corresponding aromatic aldehyde, and a step C of oxidizing this aldehyde with oxygen or an oxygen-containing gas mixture back to the aromatic peroxycarboxylic acid for re-use for epoxidizing an olefin.Type: GrantFiled: August 5, 1997Date of Patent: September 15, 1998Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Werner Schnurr, Rolf Fischer, Norbert Rieber, Michael Schulz
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Patent number: 5792878Abstract: A process for preparing chiral epoxides using chiral manganese triazanonane complexes as oxidation catalysts. These catalysts have the general formula?Mn.sub.u (L).sub.v (OR).sub.w (.mu.O).sub.x (.mu.OAc).sub.y !X.sub.Type: GrantFiled: June 28, 1996Date of Patent: August 11, 1998Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Ahmed Tafesh, Richard Walter Fischer, Bernd Scharbert
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Patent number: 5756780Abstract: Disclosed are an improvement of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl(meth)acrylate, and a stabilized 3,4-epoxycyclohexyl methyl(meth)acrylate.Type: GrantFiled: August 23, 1996Date of Patent: May 26, 1998Assignee: Daicel Chemical Industries, Ltd.Inventors: Kyuichi Ohyama, Akira Horiguchi
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Patent number: 5750741Abstract: A process for the preparation of an oxirane compound by reacting an olefinically unsaturated hydrocarbon with an organic hydroperoxide, in the presence of a catalyst comprising a titanasilsesquioxane of the general formula TiLR.sub.7 Si.sub.7 O.sub.12 and the structural formula ##STR1## wherein R is chosen from the group of cyclopentyl, cyclohexyl and cycloheptyl and L is chosen from the group of alkyl, cycloalkyl, alkylaryl, alkoxy, aryloxy, siloxy, amido and OH.Type: GrantFiled: January 15, 1997Date of Patent: May 12, 1998Assignee: Shell Oil CompanyInventors: Mark Crocker, Rudolf Henri Max Herold
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Patent number: 5705660Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.Type: GrantFiled: August 22, 1994Date of Patent: January 6, 1998Assignee: Board of Regents, University of Nebraska-LincolnInventors: David B. Berkowitz, Michelle L. Pedersen
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Patent number: 5663393Abstract: Chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed, together with methods of using such catalysts. In accordance with one aspect of the invention, the catalyst is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of, producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.Type: GrantFiled: June 6, 1995Date of Patent: September 2, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
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Patent number: 5637739Abstract: Methods of using chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed. In accordance with one aspect of the invention, the catalyst used is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.Type: GrantFiled: October 15, 1992Date of Patent: June 10, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
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Patent number: 5633391Abstract: A process for the epoxidation of olefins comprises contacting the olefin with bis(trimethylsilyl)peroxide in the presence of a rhenium catalyst in an organic solvent.Type: GrantFiled: April 12, 1996Date of Patent: May 27, 1997Assignee: National Starch and Chemical Investment Holding CorporationInventor: Steven P. Fenelli
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Patent number: 5620938Abstract: The invention relates to a catalyst for the epoxidation of alkenes using alkylhydroperoxide, the catalyst comprising an ion of one or more of the metals molybdenum, wolfram, titanium or vanadium on an inorganic carrier, characterised in that the metal ion is bound to the carrier via a polydentate organic ligand.The invention also relates to a process for the preparation of an alkene oxide by an alkene having 3 or more carbon atoms with an alkylhydroperoxide, using the catalyst described above.Type: GrantFiled: February 17, 1995Date of Patent: April 15, 1997Assignee: DSM N.V.Inventor: Otto E. Sielcken
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Patent number: 5608088Abstract: A process for producing 3,4-caranediol of the formula [I] includes subjecting 3,4-epoxycarane, which is obtained by epoxidizing 3-carene under specific conditions, to a hydration reaction in the presence of a base catalyst in aqueous ethanol under pressure to obtain 3,4-caranediol.Type: GrantFiled: September 8, 1995Date of Patent: March 4, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Keisuke Watanabe, Noboru Yamamoto, Atsushi Kaetsu, Yoshimi Yamada
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Patent number: 5599955Abstract: The present invention provides an integrated process for the production of propylene oxide from an alternate feedstream such as synthesis gas. In the process, propylene oxide is produced from a feedstream comprising hydrogen and a carbon oxide. A portion of the feedstream is passed to an oxygenate production zone to produce an oxygenate stream comprising methanol and dimethyl ether, and the oxygenate stream is passed to an olefin production zone containing a metal aluminophosphate catalyst to produce a propylene stream. The propylene stream is epoxidized with hydrogen peroxide which has been produced from hydrogen separated from a portion of the feedstream. The spent water stream produced by the epoxidation reaction is treated to remove heavy components and returned to the hydrogen peroxide production zone. The return of the unreacted propylene from the epoxidation reaction zone for its subsequent recovery and recycle permits a less complicated, lower energy propylene separation.Type: GrantFiled: February 22, 1996Date of Patent: February 4, 1997Assignee: UOPInventors: Bipin V. Vora, Peter R. Pujado
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Patent number: 5578740Abstract: Epoxy-containing compounds which are essentially free of organic halides are prepared by (I) reacting an allyl derivative of an active hydrogen-containing compound with (II) a peroxygen-containing compound. The epoxy-containing compounds are useful in coatings, castings, laminates etc.Type: GrantFiled: December 23, 1994Date of Patent: November 26, 1996Assignee: The Dow Chemical CompanyInventors: Andrew T. Au, J. Lowell Nafziger
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Patent number: 5571907Abstract: A method for producing sucrose-based epoxy monomers having one to eight epoxy groups per molecule of sucrose, which comprises reacting a mixture comprising: a sucrose monomer having an allyl-containing group on at least one of the hydroxyl groups, and a reagent or catalyst selected from molybdenum, tungsten, vanadium, titanium and peracid, in the presence of hydrogen peroxide or a derivative thereof, in relative amounts sufficient to produce a sucrose-based epoxy monomer. Monomers thus produced are also provided. The sucrose-based epoxy monomers can be cured to produce a sucrose-based epoxy resin. Such resins are useful, for example, as adhesives, composites and coatings.Type: GrantFiled: February 14, 1995Date of Patent: November 5, 1996Assignee: Hawaiian Sugar Planters' AssociationInventors: Navzer D. Sachinvala, Morton H. Litt
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Patent number: 5569773Abstract: The present invention provides a composition represented by the formula ##STR1## (wherein x is an integer of 3 to 7, y is an integer of 0 to 50, and R.sub.a and R.sub.b are H, methyl group, or propyl group and each of the R.sub.a and R.sub.b groups may be replaced with any of the other groups simultaneously) and useful as a raw material or modifier for resins for use in coating compositions, adhesives, epoxy resins, and the like, and further provides a process for producing a composition comprising compounds represented by the above formula (I) which process is characterized in that a compound represented by the formula ##STR2## is reacted with a lactone at 30.degree. to 20.degree. C. or compounds represented by the formula ##STR3## (wherein x, y, R.sub.a, and R.sub.b have the meanings as defined above) are epoxidized at 0.degree. to 80.degree. C. using a peroxide.Type: GrantFiled: July 15, 1994Date of Patent: October 29, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Tomohisa Isobe
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Patent number: 5510428Abstract: Compositions (I), (II) and (III) comprising compounds having vinyl groups as side chains and epoxidized compositions (XI), (XII) and (XIII) thereof, which can be prepared by the various reaction combinations of (a) with (b) or (b)+(c), and or (d), where(a) is at least one compound having at least one vinyl group and one epoxy group in the molecule; (b) is at least one of a polybasic compound, an anhydride thereof, a polymer having carboxylic groups at terminals and a polymer having carboxylic groups as side chains; (c) is at least one organic compound having at least one active hydrogen atom; and (d) is at east one of an unsaturated monocarboxylic compound or an unsaturated monocarboxylic ester having a hydroxyl group.Type: GrantFiled: November 21, 1994Date of Patent: April 23, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiyuki Harano, Sozo Namai, Katsuyuki Maeda, Takaaki Murai
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Patent number: 5466835Abstract: The oxidation of olefinic compounds generally using hydroperoxides, especially aqueous solutions of hydrogen peroxide, can be effected in high yield and with good selectivity in the presence of a catalyst which is a mixture of small particles of titania and a titanosilicalite. Small particle size is essential in affording a catalyst with good activity and selectivity, with particle sizes no more than about 0.3 microns being the preferred mode of operation. Dilute aqueous hydrogen peroxide solutions may be used with good results. The resulting epoxidation, even when carried out at modest temperatures and with dilute aqueous hydrogen peroxide solutions, afford superior results in epoxidation relative to TS-1.Type: GrantFiled: May 9, 1994Date of Patent: November 14, 1995Assignee: UOPInventors: Laszlo T. Nemeth, Thomas P. Malloy, Richard R. Jones
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Patent number: 5440050Abstract: A process for the production of ambergris-type labdane spiroketals of general formulae I and II ##STR1## where R represents oxygen or sulphur, useful in the perfumery industry, the said process being characterized by the intramolecular cyclisation of the epoxyketone or its thio analog of general formula III ##STR2## where R.sub.1 represents COCH.sub.3 and R.sub.2 oxygen or sulphur.Type: GrantFiled: October 18, 1994Date of Patent: August 8, 1995Assignee: Givaudan-Roure CorporationInventors: Maria do Ceu Goncalves da Costa, Maria J. V. de Oliveira Baptista Marcelo Curto, Maria R. de Loureiro da Silva Tavares da Rosa, William B. Motherwell
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Patent number: 5382676Abstract: Disclosed are the improvements of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl(meth)acrylate and 3,4-epoxyeyclohexyl methyl(meth)acrylate which is prepared by the improvements, including only minor amounts of polymers having a low molecular weight composed of 3,4-epoxycyclohexyl methyl(meth)acrylate itself.Furthermore, disclosed is a 3,4-epoxycyclohexyl methyl(meth)acrylate composition which has an excellent resistance to coloring, including a specified organic phosphorous compound.Type: GrantFiled: August 19, 1993Date of Patent: January 17, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Akihiro Kuwana, Kimihide Honda, Kunio Koga
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Patent number: 5378736Abstract: Disclosed are a composition and a process for preparation thereof, which composition comprises a novel alicyclic compound and an epoxidized compound thereof represented respectively by formulae (I) and (II) ##STR1## wherein Y.sup.1 represents at least one of the structural groups ##STR2## Y.sup.2 represents at least one of the the structural groups ##STR3## R.sup.a and R.sup.b each represent hydrogen or a methyl group, m represents a natural number of from 1 to 7, and n represents a natural number of from 1 to 20.The composition (II) is a multi-functional alicyclic epoxidized compound, which has a property of being high in epoxy group density in a molecule compared with alicyclic conventional epoxy resins, which can provide resins having wide range properties from being hard to being soft.Type: GrantFiled: May 30, 1991Date of Patent: January 3, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Shoji Watanabe, Shin Takemoto, Yoshiyuki Harano
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Patent number: 5354875Abstract: The oxidation of olefinic compounds generally using hydroperoxides, especially aqueous solutions of hydrogen peroxide, can be effected in high yield and with good selectivity in the presence of a titania-supported titanosilicate catalyst. Dilute aqueous hydrogen peroxide solutions may be used with good results. The resulting epoxidation, even when carried out at modest temperatures and with dilute aqueous hydrogen peroxide solutions, afford superior results in epoxidation relative to TS-1.Type: GrantFiled: December 23, 1993Date of Patent: October 11, 1994Assignee: UOPInventors: Laszlo T. Nemeth, Thomas P. Malloy, Richard R. Jones
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Patent number: 5331084Abstract: Fluorine-substituted epoxides of the formula ##STR1## in which the substituents R.sub.1 to R.sub.4, independently of one another, have the following meanings:R.sub.1 to R.sub.4 =H, fluorine, C.sub.1 - to C.sub.18 -alkyl in which some or all of the hydrogens may be substituted by fluorine, and at least one of the substituents R.sub.1 to R.sub.4 is a completely fluorinated alkyl or an alkyl of the formula--(CH.sub.2).sub.m --(C.sub.n F.sub.2n+1),in which m is 1 or 2, and n is an integer from 1 to 17, and x is 0 or 1.Furthermore, a method for the preparation of fluorine-substituted epoxides is described.Type: GrantFiled: February 12, 1993Date of Patent: July 19, 1994Assignee: Hoechst AktiengesellschaftInventors: Jurgen Kulpe, Heinz Strutz
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Patent number: 5329024Abstract: A method for epoxidizing olefins is provided wherein an olefin and an oxygenating agent are contacted together in the presence of a manganese complex catalyst having at least one manganese atom coordinated with a nitrogen-containing ligand such that the manganese atom to coordinated nitrogen atom is 1:3 and thereafter isolating the resultant epoxide product. Catalyst compositions are also provided formed from the adsorption of the manganese complex catalyst onto a solvent insoluble support.Type: GrantFiled: March 30, 1993Date of Patent: July 12, 1994Assignee: National Starch and Chemical Investment Holding CorporationInventors: Sharon H. Jureller, Judith L. Kerschner, Robert Humphreys
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Patent number: 5319113Abstract: The invention relates to new, liquid crystalline di(alkoxyglycidyl) compounds of optionally ring substituted 1,4-dibenzoyloxybenzenes in which an alkoxy group consisting of 2 to 8 carbon atoms is incorporated between the glycidyl groups and the 1,4-dibenzoyloxybenzene, a synthesis of 4,4'-di(hexoxyglycidyl)-(1,4-dibenzoyloxybenzene), furthermore epoxy resin mixtures containing the new dialkoxyglycidyl compounds and the epoxy resin mixtures thereof in curable mixtures.Type: GrantFiled: June 9, 1993Date of Patent: June 7, 1994Assignee: The Aerospace CorporationInventors: Joseph J. Mallon, Paul M. Adams
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Patent number: 5276235Abstract: In the co-production of propylene oxide and styrene monomer, there is produced a sodium-containing heavy residue stream previously suitable only as a low grade fuel. In accordance with the invention, the heavy residue stream is contacted with acid having a molar concentration with respect to water above that which corresponds to the product salt solubility limit, and the resulting mixture is phase separated into an aqueous sodium salt-containing slurry phase and an organic phase reduced in sodium.Type: GrantFiled: February 19, 1993Date of Patent: January 4, 1994Assignee: ARCO Chemical Technology, L.P.Inventor: Walter S. Dubner
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Patent number: 5268489Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.Type: GrantFiled: February 5, 1993Date of Patent: December 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
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Patent number: 5237076Abstract: The invention relates to new, liquid crystalline di(alkoxyglycidyl) compounds of optionally ring substituted 1,4-dibenzoyloxybenzenes in which an alkoxy group consisting of 2 to 8 carbon atoms is incorporated between the glycidyl groups and the 1,4-dibenzoyloxybenzene, a synthesis of 4,4'-di(hexoxyglycidyl)-(1,4-dibenzoyloxybenzene), furthermore epoxy resin mixtures containing the new dialkoxyglycidyl compounds and the epoxy resin mixtures thereof in curable mixtures.Type: GrantFiled: August 28, 1992Date of Patent: August 17, 1993Assignee: The Aerospace CorporationInventors: Joseph J. Mallon, Paul M. Adams
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Patent number: 5169965Abstract: A composition comprising a lactone-modified alicyclic compound (I), or an epoxidized lactone-modified alicyclic compound (II) of the following formulae: ##STR1## wherein R is an alkyl group, an aromatic group or an alkenyl group having carbon number of from 1 to 30, Y.sup.1 is at least one of the structural groups; ##STR2## Y.sup.2 is at least one of the structural group; ##STR3## X is the structural group; ##STR4## R.sup.4 and R.sup.b each independently is hydrogen or a methyl group, c and c' represent a number of from 4 to 8, from n1 to nL represents 0 or a number of more than 0, respectively, and n1+n2+n3+. . . +nL corresponds to the total mole numbers of a lactone introduced into one molecule.These compositions can be made into a heat-curable composition, a photo-curable composition, a polymerizable composition and another photo-curable composition.Type: GrantFiled: July 10, 1991Date of Patent: December 8, 1992Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Shin Takemoto, Tomohisa Isobe, Yoshiyuki Harano
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Patent number: 5151450Abstract: There are provided 4,5-Dihydroxy-2,6,6-trimethyl-2-cyclohepten-1-one, a method for preparing the same and an antiulcer agent containing the same as an effective ingredient.Type: GrantFiled: February 21, 1991Date of Patent: September 29, 1992Assignee: Tokyo Tanabe Company, LimitedInventors: Kiyokazu Murakami, Susumu Yokura
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Patent number: 5128492Abstract: An epoxidation reaction product formed by the molybdenum catalyzed reaction of propylene with tertiary butyl hydroperoxide to provide propylene oxide and tertiary butyl alcohol is separated by distillation into a propylene fraction, a propylene oxide fraction, a tertiary butyl alcohol fraction and a heavy liquid distillation fraction composed primarily of tertiary butyl hydroperoxide, tertiary butyl alcohol, dissolved molybdenum catalyst, and impurities including lower aliphatic C.sub.1 -C.sub.4 carboxylic acids, and the heavy liquid distillation fraction is saturated with hydrogen to precipitate the molybdenum therefrom for recovery.Type: GrantFiled: May 20, 1991Date of Patent: July 7, 1992Assignee: Texaco Chemical CompanyInventors: William A. Smith, Robert A. Meyer, Edward T. Marquis
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Patent number: 5101051Abstract: Epoxides are prepared by reaction of compounds containing olefinic unsaturation, for example .alpha.-olefins, terpenes and steroids, with an aliphatic diperoxydicarboxylic acid. The diperoxydicarboxylic acid contains 2 to 16 carbon atoms and suitably at least 6 carbon atoms. The process gives a good epoxidation process and does not give rise to byproduct formation.Type: GrantFiled: May 2, 1991Date of Patent: March 31, 1992Assignee: Eka NobelInventors: Harriet Ericsson, Elina Sandberg, Eva Gottberg-Klingskog
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Patent number: 4946973Abstract: The stereoselective expoxidation of cyclic 4-hydroxy olefins is disclosed. These methods involve contacting the cyclic 4-hydroxy olefin with peroxycarboximidic acid, which is preferably generated in situ by contacting an organic nitrile with aqueous hydrogen peroxide. The invention provides unexpectedly high yields of the corresponding cis-epoxides.Type: GrantFiled: September 20, 1988Date of Patent: August 7, 1990Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4921983Abstract: In the continuous epoxidation of olefins with percarboxylic acids, the alkane component which normally accumulates during the circulation of the olefin is reduced by branching off a partial current from the recycled olefin and by additional epoxidation of this olefin with percarboxylic acids as well as a subsequent separation from the epoxide.Type: GrantFiled: July 26, 1989Date of Patent: May 1, 1990Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Willi Hofen, Gunter Prescher, Helmut Maurer
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Patent number: 4882442Abstract: Process for the production of epoxides by reaction of one mol equivalent of the corresponding olefins with 1 to 2.6 mols equivalent aliphatic percarboxylic acids with 2-4 C atoms containing at least one strong acid, wherein the strong acid in the percarboxylic acid mixture is neutralized with an at least equivalent amount of an inorganic base and thereafter the percarboxylic acid mixture is combined with a reaction mixture containing the olefin, about 0.5 to about 0.74 equivalents acid-binding agent with reference to the amount of total carboxylic acid present in the percarboxylic acid mixture and, if necessary, solvent.Type: GrantFiled: January 27, 1988Date of Patent: November 21, 1989Assignee: Peroxid-Chemie GmbHInventors: Wolfgang Edl, Gunter R. Sienel
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Patent number: 4855465Abstract: Aliphatic epoxides of the formula: ##STR1## can be prepared in a technically efficient manner from the corresponding olefins by means of perpropionic acid in a benzene solution. The benzene solution can also be 1.5 weight percent of hydrogen peroxide, 1.5 weight percent of water and about 800 ppm of mineral acid.Type: GrantFiled: March 2, 1988Date of Patent: August 8, 1989Assignee: Degussa AktiengesellschaftInventors: Andreas Grund, Guenter Prescher, Georg Boehme, Willi Hofen, Heinrich Petsch
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Patent number: 4851594Abstract: Novel substituted styrene compounds of the formula ##STR1## wherein R is halogen or --CF.sub.3 ; n is an integer from 0 to 5; and X.sub.1, X.sub.2, X.sub.3, X.sub.4 and X.sub.5 are halogen, and are useful as intermediates for preparing herbicidal compounds.Type: GrantFiled: July 21, 1986Date of Patent: July 25, 1989Assignee: The Dow Chemical CompanyInventor: R. Garth Pews
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Patent number: 4851556Abstract: Epoxidized polybutadienes with an average molecular weight of 500 to 100,000 and a certain content of epoxide oxygen were prepared from the corresponding polybutadienes with use of perpropionic acid in a benzene solution. The solution can also be employed in unpurified form with maximum contents of 1.5 weight percent hydrogen peroxide 1.5 weight percent of water, and about 800 ppm of mineral acid.Type: GrantFiled: March 2, 1988Date of Patent: July 25, 1989Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Andreas Grund, Guenter Prescher, Udo Brandt
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Patent number: 4849532Abstract: The diepoxide of the formula: ##STR1## can be prepared from the corresponding diolefin in a technically simple manner by means of perpropionic acid in a benzene solution. The solution can also be employed in unpurified form with certain maximum contents of 1.5 weight percent of hydrogen peroxide, 1.5 weight percent of water, and of about 800 ppm of mineral acid.Type: GrantFiled: March 2, 1988Date of Patent: July 18, 1989Assignee: Degussa AktiengesellschaftInventors: Georg Boehme, Willi Hofen, Andreas Grund, Heinrich Petsch, Guenter Prescher
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Patent number: 4788303Abstract: A process is disclosed for preparation of novel epoxy-substituted aralkyl isocyanates by reaction of tertiary aralkyl olefins and an epoxidizing agent at a temperature of from -35.degree. C. to about 50.degree. C. The compounds are useful as intermediates to produce curing agents for polyfunctional active hydrogen-containing compounds, e.g., by reaction with polyols to produce epoxy-pendant urethanes and then with polyamines, and the like.Type: GrantFiled: December 14, 1987Date of Patent: November 29, 1988Assignee: American Cyanamid CompanyInventor: Paul S. Waterman
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Patent number: 4772733Abstract: An epoxy-sulfonylazide having the general formula ##STR1## wherein R is lower alkyl and R' is hydrogen or lower alkyl.Type: GrantFiled: September 22, 1987Date of Patent: September 20, 1988Assignee: Hercules IncorporatedInventor: Anthony B. Clayton
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Patent number: 4724031Abstract: 2,6-Disubstituted 4-epoxypropyl glycidyl ethers of the formula ##STR1## wherein X is a group R' or X is a group of the formula ##STR2## and each of R and R' independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, a halogen atom or C.sub.6 -C.sub.10 aryl, can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for application in the electronics industry, or as adhesives. Compounds of the formula are also valuable reactive diluents for curable epoxy resin mixtures.Type: GrantFiled: June 4, 1986Date of Patent: February 9, 1988Assignee: Ciba-Geigy CorporationInventors: Charles E. Monnier, Sheik Abdul-Cader Zahir, Sameer H. Eldin
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Patent number: 4723038Abstract: Processes for preparing compounds which exhibit seed germinating activity are disclosed. An ester of acetoacetic acid is condensed with a ketone to produce a substituted cyclohexenone which is reacted with a thiol to get a dithioketal which is then desulfurized to produce an ester of a substituted cyclohex-2-ene-1-carboxylic acid which exhibits seed germinating activity. The same compound can be produced by a different process which reacts the substituted cyclohexenone with a reducing agent. An exemplary reducing agent would be an organosilane and a Lewis acid.Type: GrantFiled: December 31, 1985Date of Patent: February 2, 1988Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Oliver D. Dailey, Jr.
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Patent number: 4717771Abstract: 2,3-Epoxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone, an epoxy ketone of formula ##STR1## possesses useful fragrance characters and, consequently, it can be used advantageously in the manufacture of perfume, perfume bases and perfumed products. It develops a flowery and fruity odor.Type: GrantFiled: October 4, 1985Date of Patent: January 5, 1988Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Dietrich Kastner
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Patent number: 4647678Abstract: The epoxidation of terminally and/or internally olefinically unsaturated hydrocarbon compounds which are liquid at 50.degree. to 100.degree. C. and at atmospheric pressure (oil phase), in which the oil phase is treated with an acid phase containing acetic acid, hydrogen peroxide and peracetic acid in aqueous solution, after which the aqueous acid phase is separated from the oil phase, the peracetic acid in the aqueous acid phase is regenerated and the regenerated aqueous acid phase is returned to the epoxidation reactor. Epoxidation is carried out using an aqueous acid phase containing at most about 10% by weight of peracetic acid, and the peracetic acid content in the aqueous acid phase is reduced by at most about 50%, based on the peracetic acid content of the aqueous acid phase used, after a single passage through the epoxidation stage. After separation from the oil phase, the aqueous acid phase preferably is cooled before regeneration.Type: GrantFiled: December 26, 1985Date of Patent: March 3, 1987Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Klemens Eckwert, Lutz Jeromin, Alfred Meffert, Eberhard Peukert, Bernhard Gutsche
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Patent number: 4611070Abstract: Dye-forming components of the general formula ##STR1## where A is the radical of a fused benzo ring or 2,1-naphthalene ring, and either radical may be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro, chlorine, bromine or C.sub.1 -C.sub.6 -alkoxycarbonyl, R.sup.1 is C.sub.1 -C.sub.16 -alkyl, C.sub.7 -C.sub.10 -phenylalkyl or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine or bromine, and R.sup.2 and R.sup.3 independently of one another are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.4 -alkyl, which is substituted by cyano, chlorine, methoxy or ethoxy, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.7 -C.sub.10 -phenylalkyl or trimethylene which is unsubstituted or substituted by 1, 2 or 3 methyl groups and is bonded to the carbon in the 6- and/or 8-position of the benzo ring, or R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is phenyl which is unsubstituted or substituted by chlorine, bromine, C.sub.1 -C.sub.Type: GrantFiled: January 4, 1982Date of Patent: September 9, 1986Assignee: BASF AktiengesellschaftInventor: Andreas Oberlinner
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Patent number: 4607113Abstract: Production of novel molybdenum dioxo dialkyleneglycolate compositions, especially adapted for use as catalysts in the epoxidation of olefinic compounds with an organic hydroperoxide, by reaction of molybdenum trioxide with particular dialkylene glycol compounds at specified elevated temperatures while removing water.Type: GrantFiled: November 5, 1984Date of Patent: August 19, 1986Assignee: Atlantic Richfield CompanyInventors: Wilfred P. Shum, Charles F. Cooper