Carbon To Carbon Unsaturation Containing Patents (Class 568/616)
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Patent number: 6642423Abstract: Ethoxylations of various initiator compounds are performed in the presence of metal cyanide catalysts. The catalysts surprisingly form a wide variety of polyether products that in most cases contain only small amounts of high molecular weight poly(ethylene oxide).Type: GrantFiled: April 24, 2002Date of Patent: November 4, 2003Assignee: Dow Global Technologies, Inc.Inventors: Katherine S. Clement, Louis L. Walker, Richard M. Wehmeyer, Robert H. Whitmarsh, David C. Molzahn, William P. Dianis, David E. Laycock, John W. Weston, Richard J. Elwell
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Publication number: 20030199655Abstract: The present invention provides a reactive diluent composition which overcomes drawbacks of both the radical-cure and the cationic-cure reactive diluents and can be applied in a broad variety of uses such as paints, inks, adhesives, pressure sensitive adhesives, surface-modifiers, and molding materials; a curable resin composition containing the same; an activated energy ray-curable resin composition; and an activated energy ray-curable ink composition for ink-jet printing.Type: ApplicationFiled: April 19, 2002Publication date: October 23, 2003Applicant: NIPPON SHOKUBAI CO., LTD.Inventors: Keiji Yurugi, Akihiko Fukada, Kenji Matsukawa
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Patent number: 6576799Abstract: A process for preparing an ether-capped poly(oxyalkylated) alcohol surfactant which results in the absence of metallic catalyst component residues from the ether-capped poly(oxyalkylated) alcohol surfactant.Type: GrantFiled: May 4, 2001Date of Patent: June 10, 2003Assignee: The Procter & Gamble CompanyInventors: Larry Eugene Miller, Donald Eugene Levengood, Mark Robert Sivik, Bernard William Kluesener, Terry Franklin Formyduval
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Patent number: 6573412Abstract: The invention provides chain-coupled polymeric alkoxide compounds for use as the elastomeric component in vulcanizable elastomeric compositions comprising silica, carbon black or mixtures thereof. In particular, the invention provides anionically polymerized polymers having polymer chain living ends that are functionalized with alkoxide groups and coupled together by a metal or nonmetal atom. The polymeric alkoxide compounds have an initial high viscosity for ease of handling prior to compounding, a stable viscosity during storage, and a decreased compound viscosity for better filler dispersion and improved mixing efficiency. The invention further provides a pneumatic tire having at least one component produced from the vulcanizable elastomeric composition of the invention.Type: GrantFiled: May 12, 2000Date of Patent: June 3, 2003Assignee: Bridgestone CorporationInventors: Terrence E. Hogan, William L. Hergenrother, James E. Hall
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Patent number: 6570041Abstract: Disclosed is a high heat resistance and low viscosity polyoxytetramethylene glycol (PTMG) having the following characteristics (1) to (4): (1) a number average molecular weight of from 500 to 3000; (2) a molecular weight distribution of 1.8 or less in terms of the Mw/Mn ratio; (3) a content of high molecular weight PTMG molecules of from 2 to 5% by weight, wherein the high molecular weight PTMG molecules are PTMG molecules having molecular weights which are at least six times as large as the number average molecular weight of all PTMG molecules; and (4) a heteropolyacid content of from 10 to 900 ppb by weight.Type: GrantFiled: January 22, 2002Date of Patent: May 27, 2003Assignee: Asahi Kasei Kabushiki KaishaInventors: Tamotsu Kodama, Takeshi Mori, Takaharu Akedo
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Patent number: 6531636Abstract: The present invention relates to a compound of the general formula (I) which is a non-hydrolysable analogue of endogenous cannabinoids, which are found to be more potent therapeutic agents as they are more stable, for example, to hydrolytic cleavage in the gastrointestinal tract. The cannabinoid analogues of the invention have a therapeutic value. Therefore, pharmaceutical compositions comprising as active ingredient a therapeutically effective amount of at least one compound of the invention may be prepared. Such compositions may be used as anti-inflammatory, anti-asthmatic, analgetic, hypotensive, antiemetic or anti-spasmodic compositions, and as compositions for treating and/or preventing glaucoma or migraine, or as compositions for relieving symptoms of multiple sclerosis and mood stimulating compositions.Type: GrantFiled: October 3, 2000Date of Patent: March 11, 2003Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventors: Raphael Mechoulam, Esther Fride, Shimon Ben Shabat, Tzviel Sheskin, Aviva Breuer
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Patent number: 6495727Abstract: A process for preparing an ether-capped poly(oxyalkylated) alcohol surfactant having the formula R1O[CH2CH(R3)O]xCH2CH(OH)CH2OR2 wherein R1 and R2 are linear or branched, saturated or unsaturated, aliphatic or aromatic hydrocarbon radicals having from 1 to about 30 carbon atoms; R3 is H, or a linear aliphatic hydrocarbon radical having from 1 to about 4 carbon atoms; x is an integer having an average value from 1 to about 30, wherein when x is about 2 or greater R3 may be the same or different; further wherein when x is about 15 or greater and R3 is H and methyl, at least four of R3 are methyl, further wherein when x is about 15 or greater and R3 includes H and from 1 to 3 methyl groups, then at least one R3 is ethyl, propyl or butyl, further wherein R2 can optionally be alkoxylated, wherein said alkoxy is selected from ethoxy, propoxy, butoxy and mixtures thereof; said process comprising the steps of: (b) providing a glycidyl ether having the formula: wherein R2 is defineType: GrantFiled: May 4, 2001Date of Patent: December 17, 2002Assignee: The Procter & Gamble CompanyInventors: Glenn Thomas Jordan, IV, Larry Eugene Miller, Donald Eugene Levengood, Mark Robert Sivik, Bernard William Kluesener, Terry Franklin Formyduval, Deborah Jean Back
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Publication number: 20020188089Abstract: Alkoxylated acrylate and methacrylate macromonomers are disclosed that are useful in the preparation of water-reducing additives for concrete, ultraviolet light-curable adhesives, and water-dispersed polyurethanes. The macromonomers are suitably prepared by alkoxylating a hydroxyalkylacrylate or hydroxyalkylmethacrylate in the presence of a DMC catalyst using the continuous addition of starter (CAOS) in order to prevent the formation of by-products during the fabrication of the macromonomer.Type: ApplicationFiled: February 20, 2001Publication date: December 12, 2002Inventor: Jianzhong Shen
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Patent number: 6482993Abstract: This invention relates to a process for the production of long-chain polyether polyols without working up, in which oligomeric, alkoxylated starter compounds having molecular weights of 200 to 1000 are first obtained by catalysis with perfluoroalkylsulfonates of the metals of group III A of the periodic system of elements (in accordance with the IUPAC convention of 1970) from low molecular weight starters by reaction with alkylene oxides at reaction temperatures of 80 to 200° C. and catalyst concentrations of 5 to 200 ppm, which oligomeric, alkoxylated starter compounds are then converted without working up and removal of the catalyst by means of highly active DMC catalysts at a catalyst concentration of 30 ppm or below, relative to the quantity of polyether polyol to be produced, by reaction with alkylene oxides into higher molecular weight, long-chain polyether polyols.Type: GrantFiled: October 18, 2000Date of Patent: November 19, 2002Assignee: Bayer AktiengesellschaftInventors: Jörg Hofmann, Pramod Gupta
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Patent number: 6482994Abstract: Ether-capped poly(oxyalkylated) alcohol surfactants having superior grease cleaning abilities and improved spotting/filming benefits are provided.Type: GrantFiled: February 2, 2000Date of Patent: November 19, 2002Assignee: The Procter & Gamble CompanyInventors: William Michael Scheper, Mark Robert Sivik
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Patent number: 6455234Abstract: This invention provides water-based compositions, particularly coating, ink, fountain solution and agricultural compositions, manifesting reduced equilibrium and dynamic surface tension by the incorporation of a surface tension reducing amount of an acetylenic diol ethylene oxide/propylene oxide adduct of the structure where r and t are 1 or 2, (n+m) is 1 to 30 and (p+q) is 1 to 30. Use of such adducts as surfactants in photoresist developer/electronics cleaning compositions is particularly advantageous. Also disclosed is a method for making random and block EO/PO adducts of acetylenic diols by reacting an acetylenic diol with EO and/or PO in the presence of a trialkylamine or Lewis acid.Type: GrantFiled: December 18, 2001Date of Patent: September 24, 2002Assignee: Air Products and Chemicals, Inc.Inventors: Kevin Rodney Lassila, Paula Ann Uhrin, Joel Schwartz
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Publication number: 20020128520Abstract: A process for the preparation of 1,1,4,4-tetramethoxy-2-butene by reacting 2,5-dimethoxydihydrofuran with methanol in the presence of acids comprises carrying out the reaction in the presence of solid catalysts having acidic centers.Type: ApplicationFiled: March 19, 2002Publication date: September 12, 2002Inventors: Christoph Wegner, Joachim Paust, Hansgeorg Ernst
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Patent number: 6444858Abstract: The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form during transport to said reaction vessel, during discharge into said reaction vessel, and during contacting of the organic compound with the alkylene oxide. The result is an alkoxylated product containing less flocculant.Type: GrantFiled: April 19, 1999Date of Patent: September 3, 2002Assignee: Baker Hughes IncorporatedInventor: Philip Leung
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Patent number: 6429342Abstract: Ethoxylations of various initiator compounds are performed in the presence of metal cyanide catalysts. The catalysts surprisingly form a wide variety of polyether products that in most cases contain only small amounts of high molecular weight poly(ethylene oxide).Type: GrantFiled: July 7, 2000Date of Patent: August 6, 2002Assignee: Dow Global Technologies Inc.Inventors: Katherine S. Clement, Louis L. Walker, Richard M. Wehmeyer, Robert H. Whitmarsh, David C. Molzahn, William P. Dianis, David E. Laycock
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Patent number: 6395938Abstract: A method for controlling the molecular weight distribution of polyether glycol in producing polyether glycol having a specified number average molecular weight by polymerizing tetrahydrofuran as a starting monomer with the use of a heteropoly-acid as a catalyst, which method comprises conducting the polymerization in the presence of an amount of water which can form two phases of the organic phase and a catalyst phase, sampling the polymerization product during the polymerization to determine the molecular weight distribution and, when the molecular weight distribution thus found is narrower than the specified molecular weight distribution, making the residence time distribution of the starting monomer in the catalyst phase wider, while, when the found molecular weight distribution is wider than the specified molecular weight distribution, making the residence time distribution of the starting monomer in the catalyst phase narrower.Type: GrantFiled: November 22, 2000Date of Patent: May 28, 2002Assignee: Asahi Kasei Kabushiki KaishaInventor: Takaharu Akedo
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Patent number: 6391820Abstract: The invention relates to novel double-metal cyanide catalysts for the preparation of polyether polyols by polyaddition of alkylene oxides to starter compounds containing active hydrogen atoms, wherein the catalyst contains a) double metal cyanide compounds, b) organic complex ligands other than c), and c) glycoside. The catalysts according to the invention have greatly increased activity in the preparation of polyether polyols.Type: GrantFiled: January 23, 2001Date of Patent: May 21, 2002Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Jörg Hofmann, Pramod Gupta, Walter Schäfer
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Publication number: 20020055660Abstract: This invention provides water-based compositions, particularly coating, ink, fountain solution and agricultural compositions, manifesting reduced equilibrium and dynamic surface tension by the incorporation of a surface tension reducing amount of an acetylenic diol ethylene oxide/propylene oxide adduct of the structure 1Type: ApplicationFiled: October 11, 2001Publication date: May 9, 2002Inventors: Kevin Rodney Lassila, Paula Ann Uhrin
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Patent number: 6384216Abstract: A process for purifying alkenyl compounds having a divalent or trivalent heteroatom in the &agr;-position relative to the double bond by distillation comprises carrying out at least two distillations in which the purified alkenyl compounds are obtained from the gas phase by condensation, where the time between the first distillation after the synthesis of the alkenyl compounds and at least one further distillation is at least one day and the purified alkenyl compounds have an APHA color number of <30.Type: GrantFiled: August 9, 2001Date of Patent: May 7, 2002Assignee: BASF AktiengesellschaftInventors: Rudolf Erich Lorenz, Arnd Böttcher, Rolf Pinkos
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Patent number: 6372927Abstract: The process for preparing an alkylene oxide adduct, including the steps of feeding an organic compound having active hydrogen and an alkylene oxide to a reaction column packed with a solid catalyst, and carrying out addition reaction of the organic compound having active hydrogen with an alkylene oxide in a gas-liquid fixed bed reaction, wherein the alkylene oxide is in a state of gas and the organic compound having active hydrogen is in a state of liquid.Type: GrantFiled: August 10, 1998Date of Patent: April 16, 2002Assignee: Kao CorporationInventors: Nobuhiro Tatsumi, Yoshikazu Ogura, Takanobu Katayama, Osamu Tabata
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Patent number: 6365785Abstract: A process for preparing an ether-capped poly(oxyalkylated)alcohol surfactant is provided.Type: GrantFiled: February 2, 2000Date of Patent: April 2, 2002Assignee: TherProcter & Gamble CompanyInventor: Mark Robert Sivik
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Patent number: 6355845Abstract: Certain alcohol initiators containing unconjugated carbon-carbon double bonds can be alkoxylated with excellent efficiency and low production of by-products using a metal cyanide catalyst.Type: GrantFiled: July 7, 2000Date of Patent: March 12, 2002Assignee: The Dow Chemical CompanyInventors: Katherine S. Clement, Louis L. Walker, Richard M. Wehmeyer, Wanda W. Rauscher, Robert H. Whitmarsh
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Patent number: 6300526Abstract: Hydro-2,2-difluoroalkylvinylethers having the formula CF2═CH—O—RA (I) wherein RA is a radical containing fluorine, optionally containing halogens such as Cl, Br, I, hydrogen, functional groups CM, COOR′, CON(R′)2, SO2OR′, m wherein R′ is a C1-C5 alkyl, RA being selected from the following: a linear or branched, saturated or unsaturated C2-C20 fluoroalkyl, or a saturated or unsaturated C4-C6 fluorinated cyclic group wherein optionally from 1 to 2 carbon atoms are substituted with oxygen atoms, or a linear, branched saturated or unsaturated, C3-C15 fluorooxyalkyl group, containing one or Core oxygen atoms.Type: GrantFiled: July 29, 1999Date of Patent: October 9, 2001Assignee: Austmont S.p.A.Inventors: Walter Navarrini, Antonio Russo
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Patent number: 6255536Abstract: The present invention describes a novel process for the preparation of perfluorovinyl ethers. The process involves providing a hydrocarbon precursor that may be partially halogenated, fluorinating the precursor to provide a perfluorinated intermediate, and converting the perfluorinated intermediate to the desired perfluorinated ether. Novel perfluorovinyl ethers are also provided.Type: GrantFiled: December 22, 1999Date of Patent: July 3, 2001Assignees: Dyneon LLC, 3M Innovative Properties CompanyInventors: Allan T. Worm, George G. I. Moore, Miguel A. Guerra, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Erik D. Hare
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Patent number: 6248889Abstract: A process for preparing a fluoride from its corresponding alcohol comprises the steps of (a) forming a mixture comprising (i) at least one fluorinated, saturated aliphatic or alicyclic sulfonyl fluoride (for example, perfluorobutanesulfonyl fluoride) and (ii) at least one primary or secondary alcohol; and (b) adding a molar excess of at least one strong, aprotic, non-nucleophilic, hindered, double bond-containing, organic base (for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) to the mixture.Type: GrantFiled: November 20, 1998Date of Patent: June 19, 2001Assignee: 3M Innovative Properties CompanyInventors: Patricia M. Savu, Daniel C. Snustad
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Patent number: 6093855Abstract: The divinyl ethers of diethylene glycol or triethylene glycol are separated from the monovinyl ether of the corresponding oligoethylene glycol by distillation, a metal hydroxide being added to the vinyl ether mixture.Type: GrantFiled: September 23, 1998Date of Patent: July 25, 2000Assignee: BASF AktiengesellschaftInventor: Rudolf Erich Lorenz
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Patent number: 6028229Abstract: A process for the production of end-capped nonionic surfactants corresponding to formula (I): ##STR1## in which R.sup.1 is an alkyl or alkenyl group containing 6 to 22 carbon atoms, n1 and n2 independently of one another represent 0 or a number from 1 to 10, m represents a number from 1 to 20 and R.sup.2 represents methyl or ethyl, by(a) etherifying a fatty alcohol polyglycol ether corresponding to formula (II): ##STR2## in which R.sup.1, n1, n2 and m are as defined above, with a dialkyl sulfate in the presence of a solid substantially water-free base and an alkali metal or alkaline earth metal hydride,(b) adding water to the crude ethers in such a quantity that phase separation occurs, and(c) removing the organic phase.Type: GrantFiled: August 11, 1997Date of Patent: February 22, 2000Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Joaquim Bigorra Llosas, Nuria Bonastre, Rafael Pi Subirana, Antonio Trius Oliva
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Patent number: 5990232Abstract: Unique, well defined polyethers containing both hydroxyl-functionality and unsaturation-functionality are prepared by oxyalkylating an unsaturated monomer having at least two free carboxylic acid groups in the presence of an effective amount of a double metal cyanide complex catalyst, optionally, when necessary, in the presence of a free radical polymerization inhibitor. The resulting polyethers are eminently suitable for such uses as polymer polyol stabilizers or stabilizer precursors, and both in situ and ex situ impact modifiers for thermoplastics.Type: GrantFiled: August 25, 1997Date of Patent: November 23, 1999Assignee: ARCO Chemical Technology, L.P.Inventors: Jianzhong Shen, Kenneth G. McDaniel, John E. Hayes, Uli B. Holeschovsky, Harry R. Hinney
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Patent number: 5965778Abstract: Elastomers exhibiting decreased demold times and improved green strength are prepared by reacting a di- or polyisocyanate with a monodisperse polyoxypropylene diol having ultra-low unsaturation, and preferably prepared by the double metal cyanide.t-butyl alcohol catalyzed polymerization of propylene oxide. Further improved demold times and elevated elastomer physical properties are made possible by the use of multidisperse polyoxyalkylene polyether polyol blends having an overall unsaturation of less than 0.010 meq/g and a polydispersity of about 1.4 or greater.Type: GrantFiled: August 31, 1998Date of Patent: October 12, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Gary L. Allen, Nigel Barksby, Stephen D. Seneker, Usama E. Younes
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Patent number: 5939590Abstract: Tetrahydrofuran/but-2-yne-1,4-diol copolymers containing C--C triple bonds and having an average molecular weight M.sub.n of from 500 to 3500 Dalton and a content of from 0.5 to 3 mol of triple bonds/mol of copolymer and blends of these copolymers with polytetrahydrofuran having an average molecular weight M.sub.n of from 500 to 3500 Dalton, processes for their preparation and their use.Type: GrantFiled: August 26, 1997Date of Patent: August 17, 1999Assignee: Basf AktiengesellschaftInventors: Christoph Sigwart, Rolf Fischer, Rainer Becker, Klaus-Dieter Plitzko, Gerd Heilen, Christof Palm, Peter Groll
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Patent number: 5929290Abstract: A novel polymerizable surfactant represented by the general formula (1): ##STR1## (wherein, R.sup.1 represents a hydrogen atom or a methyl group, Rf represents a hydrocarbon group in which one or more hydrogen atoms are replaced by a fluorine atom or atoms, or an acyl group in which one or more hydrogen atoms are replaced by a fluorine atom or atoms, AO and AO' represent a group selected from an oxyalkylene group having 2-4 carbon atoms or a styrene oxide residue, m and m' are 0 or a number between 1 and 1,000, X represents a hydrogen atom or a hydrophilic group).Type: GrantFiled: September 29, 1997Date of Patent: July 27, 1999Assignee: Asahi Denka Kogyo K. K.Inventors: Kaoru Komiya, Hiromasa Kawamata, Shohei Umezawa
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Patent number: 5885952Abstract: A detergent base which is obtainable from the reaction of an ethylenically unsaturated sulfonic acid or carboxylic acid or anhydride thereof with a nonionic surfactant of the formulaR.sub.1 --O-(alkylene-O).sub.n.sbsb.1 --R.sub.2 (1)in whichR.sub.1 is C.sub.8 -C.sub.22 alkyl or C.sub.8 -C.sub.18 alkenyl;R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, a cycloaliphatic radical having at least 6 C atoms or benzyl; andn.sub.1 is a number from 1 to 60;and if appropriate with sugar derivatives.The detergent base has a good calcium-dispersing power, is very stable to electrolytes and heat and has an excellent washing action and anti-redeposition properties. It is therefore suitable for the preparation of powder and liquid detergents.Type: GrantFiled: May 15, 1996Date of Patent: March 23, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Rolf Kuratli, Claude Eckhardt, Frank Bachmann, Werner Schreiber
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Patent number: 5714638Abstract: Polyoxyalkylene glycol monoethers of monohydric alcohols are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerized in the absence of water and in the presence of a monohydric alcohol and of an anhydrous heteropoly acid catalyst.Type: GrantFiled: February 1, 1995Date of Patent: February 3, 1998Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5659068Abstract: Polyoxyalkylene glycol monoesters of carboxylic acids are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerized in the absence of water and in the presence of a carboxylic acid and of an anhydrous heteropolyacid catalyst.Type: GrantFiled: May 31, 1994Date of Patent: August 19, 1997Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5650544Abstract: The present invention provides a process for producing an unsaturated ether, which comprises subjecting a glycol ether to intramolecular dehydration in a gas phase in the presence of a catalyst to convert the glycol ether into an unsaturated ether directly in a one-step reaction. As the catalyst, an oxide containing, for example, silicon and an alkali metal is used. The process, which uses no auxiliary raw material, can produce an unsaturated ether (a vinyl ether and/or an allyl ether) simply and safely without generating any waste material derived from the auxiliary raw material.Type: GrantFiled: September 15, 1995Date of Patent: July 22, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Kimio Ariyoshi, Yuuji Shimasaki
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Patent number: 5650543Abstract: This invention relates to ethoxylated acetylenic glycol compositions represented by the formula: ##STR1## wherein m and n are integers and the sum is from 4-12. These ethoxylated acetylenic diols are excellent as surfactants alone or admixed with other surfactants for use in water borne coatings.Type: GrantFiled: August 31, 1995Date of Patent: July 22, 1997Assignee: Air Products and Chemicals, Inc.Inventor: Steven Wayne Medina
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Patent number: 5616679Abstract: A polyalkylene glycol having the general formula:HO--[R--O--].sub.n Hin which n has a value of at least 2 and R is an alkylene radical containing at least 20 carbon atoms is provided. Preferred polyalkylene glycols have an alkylene radical which is a branched alkylene radical containing at least 10 carbon atoms in the main chain and a degree of polymerization such that n is from 4 to 7. The polyalkylene glycol is prepared by the acid-catalyzed polycondensation of a monomeric alkylene glycol at elevated temperature.Type: GrantFiled: November 14, 1995Date of Patent: April 1, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Matthias Fies, Roland Gr utzmacher, Alfred Westfechtel
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Patent number: 5608117Abstract: Disclosed are novel saturated polyether compounds comprised of n units of residue (1) and m units of residue (2), wherein (i) residues (1) and (2) have the structures: ##STR1## (ii) the total value of n+m is 2 to 70 and m/(n+m) is 0.05 to 0.98; (ii) at least 98 percent of the terminal hydroxyl groups of the polyether have the structure: ##STR2## The polyethers are obtained by first polymerizing 3,4-epoxy-l-butene to produce unsaturated polyether precursors comprising residues (1A) and (2A) having the structures: ##STR3## and then hydrogenating the unsaturated polyether precursors. The hydrogenation advantageously is performed in the presence of a nickel hydrogenation catalyst.Type: GrantFiled: August 28, 1995Date of Patent: March 4, 1997Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Stephen N. Falling
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Patent number: 5567858Abstract: Propenyl ether monomers of formula VA(OCH.dbd.CHCH.sub.3).sub.nwherein n is an integer from one to six and A is selected from cyclic ethers, polyether and alkanes are disclosed. The monomers are readily polymerized in the presence of cationic photoinitiators, when exposed to actinic radiation, to form poly(propenyl ethers) that are useful for coatings, sealants, varnishes and adhesives. Compositions for preparing polymeric coatings comprising the compounds of formula V together with particular cationic photoinitiators are also disclosed, as are processes for making the monomers from allyl halides and readily available alcohols. The process involves rearranging the resulting allyl ethers to propenyl ethers.Type: GrantFiled: December 12, 1995Date of Patent: October 22, 1996Assignee: Rensselaer Polytechnic InstituteInventor: James V. Crivello
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Patent number: 5536882Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of an acidic catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, n/(n+m) is a value in the range of 0.70 to 0.Type: GrantFiled: March 3, 1995Date of Patent: July 16, 1996Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Stephen N. Falling
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Patent number: 5468796Abstract: In the manufacture of soft tissue products such as facial and bath tissue, a creping adhesive composition comprising from about 0.05 to about 20 dry weight percent of an ethoxylated acetylenic diol has been found to reduce skulch, improve creping blade life, and improve crepe quality. The creping adhesive composition is particularly useful for creping throughdried tissue webs.Type: GrantFiled: August 17, 1994Date of Patent: November 21, 1995Assignee: Kimberly-Clark CorporationInventors: Franklin M. C. Chen, Frank G. Druecke
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Patent number: 5466759Abstract: Disclosed are novel saturated polyether compounds comprised of n units of residue (1) and m units of residue (2), wherein (i) residues (1) and (2) have the structures: ##STR1## (ii) the total value of n+m is 2 to 70 and m/(n+m) is 0.05 to 0.98; (ii) at least 98 percent of the terminal hydroxyl groups of the polyether have the structure: ##STR2## The polyethers are obtained by first polymerizing 3,4-epoxy-1-butene to produce unsaturated polyether precursors comprising residues (1A) and (2A) having the structures: ##STR3## and then hydrogenating the unsaturated polyether precursors. The hydrogenation advantageously is performed in the presence of a nickel hydrogenation catalyst.Type: GrantFiled: October 24, 1994Date of Patent: November 14, 1995Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Stephen N. Falling
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Patent number: 5457241Abstract: This invention relates to the polyalk-1-enyl ethers having the formula ##STR1## which is the reaction product of a hydroxylated compound and an alk-1-enyloxy oxirane and to the process for preparing the polyalk-1-enyl ether product.Type: GrantFiled: January 5, 1994Date of Patent: October 10, 1995Assignee: ISP Investments Inc.Inventors: Jeffrey S. Plotkin, Kolazi S. Narayanan, Paul D. Taylor
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Patent number: 5451652Abstract: Propoxylated allyl alcohol homopolymers and copolymers of allyl alcohol and propoxylated allyl alcohol are disclosed. The polymers are soluble in many organic solvents, making them useful in a variety of applications, including polyesters, polyurethanes, alkyds, uralkyds, polyamines, acrylates, crosslinked polymeric resins, and polymer blends.Type: GrantFiled: April 28, 1994Date of Patent: September 19, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Shao-Hua Guo, Robert G. Gastinger
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Patent number: 5434314Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of an acidic catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, n/(n+m) is a value in the range of 0.70 to 0.Type: GrantFiled: January 18, 1994Date of Patent: July 18, 1995Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Stephen N. Falling
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Patent number: 5416240Abstract: Polyoxyalkylene glycols are prepared by a process in which tetrahydrofuran is polymerized with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals in the absence of water and in the presence of a monohydric alcohol or of a monocarboxylic acid with the aid of an anhydrous heteropoly acid catalyst, and the polyoxyalkylene glycol is liberated from the resulting polyoxyalkylene glycol monoethers or polyoxyalkylene glycol monoesters by cleavage of the monoether or monoester bond.Type: GrantFiled: March 2, 1993Date of Patent: May 16, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Franz Merger, Herbert Mueller
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Patent number: 5414143Abstract: Polyoxyalkylene glycol monoethers of monohydric alcohols are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerised in the absence of water and in the presence of a monohydric alcohol and of an anhydrous heteropoly acid catalyst.Type: GrantFiled: March 2, 1993Date of Patent: May 9, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5371253Abstract: Esterified alkoxylated mono- and diglycerides suitable for use as reduced calorie fat substitutes in food products may be produced by alkoxylating a tertiary alkyl partial ether of glycerin with an epoxide and then reacting the alkoxylated glycerin tertiary alkyl partial ether thereby obtained with a fatty acid under acid-catalyzed conditions. Separate deprotection and esterification steps are not required, resulting in a considerably streamlined process as compared to alternative methods of synthesizing alkoxylated fat substitutes having one or two fatty acid acyl groups attached directly to glycerin.Type: GrantFiled: December 14, 1993Date of Patent: December 6, 1994Assignee: Arco Chemical Technology, L.P.Inventor: Charles F. Cooper
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Patent number: 5362832Abstract: A compound of the formula ##STR1## where R, which may be the same or different, is selected from at least one of hydrogen, methyl, ethyl and phenyl, at least one R on each --OCHR--CHR-- unit being hydrogen; where m is an integer selected from 1-100; where n is an integer selected from 8 and 9. The preferred process of preparation is by the reaction of alkylene oxide with linoleyl alcohol in the presence of a catalyst which is a Bronsted base.The compounds are useful as reactive surfactants in aqueous emulsion polymerisation processes.Type: GrantFiled: September 3, 1992Date of Patent: November 8, 1994Assignee: ICI Australia Operations Proprietary LimitedInventor: Iain Cook
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Patent number: 5334772Abstract: This invention relates to the polyalk-1-enyl ethers having the formula ##STR1## which is the reaction product of a hydroxylated compound and an alk-1-enyloxy oxirane and to the process for preparing the polyalk-1-enyl ether product.Type: GrantFiled: April 13, 1992Date of Patent: August 2, 1994Assignee: ISP Investments Inc.Inventors: Jeffrey S. Plotkin, Kolazi S. Narayanan, Paul D. Taylor
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Patent number: 5276204Abstract: Fatty alcohol mixtures R.sub.mix --OH of natural and, in particular, purely vegetable origin and ethoxylates thereof showing improved low-temperature behavior and corresponding to the general formula R.sub.mix --O--(CH.sub.2 CH.sub.2 O).sub.x --H, in which x is a number of 2 to 10 and R.sub.mix represents selected mixtures of saturated and olefinically unsaturated fatty alcohol hydrocarbon radicals in the C 6-20 or C 12-20 ranges correspond to specification I for the chain length range R.sub.mix --=6-20 and to specification II for the chain length range R.sub.mix --=C 12-20:______________________________________ Specification I II structurally analogous to % by weight ______________________________________ C 6 caproic acid 0.1-0.6 -- C 8 caprylic acid 2.5-10 -- C 10 capric acid 2.5-14 -- C 12 lauric acid 37-52 39-69 C 14 myristic acid 10-20 10-27 C 16 palmitic acid 6-10 6-14 C 18 stearic acid 1-5 1-7 C 18' oleic acid 5-23 6-31 C 18" linoleic acid 1-4 1-6 C 18"' linolenic acid 0.1-1 0.1-2 C 20 arachic acid 0.Type: GrantFiled: October 23, 1992Date of Patent: January 4, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karl-Heinz Schmid, Hans Peter Kubersky, Guenter Demmering, Alfred Meffert