Polyhydroxy Containing Patents (Class 568/623)
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Patent number: 6204357Abstract: The invention is directed to new double metal cyanide (DMC) catalysts, a process for the preparation of these catalysts, and to a process for the preparation of polyetherpolyols by the polyaddition of alkylene oxides to starter compounds which contain active hydrogen atoms, wherein the catalyst comprises the novel double metal cyanide (DMC) catalyst of the present invention. These new double metal cyanide (DMC) catalysts comprise a) one or more double metal cyanide compounds, b) one or more organic complex ligands, and c) one or more cyclodextrins, with the proviso that b) and c) are different compounds. The catalysts of this invention exhibit greatly increased activity during preparation of a polyetherpolyol.Type: GrantFiled: February 10, 2000Date of Patent: March 20, 2001Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Jörg Hofmann, Pramod Gupta, Lambertus Groenendaal
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Patent number: 6191315Abstract: Most generally, the invention provides a method for making a neutralized polyether polyol, comprising the steps of a) Polymerizing one or more alkylene oxides in the presence of an alkaline catalyst to form a polyalkylene oxide intermediate; and b) Neutralizing the intermediate, after the polymerization step a) is complete, with an organic acid of general formula where R1 is hydrogen, methyl, or ethyl; R2 is methyl or ethyl; and R3 is an alkyl, aryl, or aralkyl group containing one to twelve carbon atoms. The invention also comprises the novel compositions made by the above process.Type: GrantFiled: February 11, 1999Date of Patent: February 20, 2001Assignee: BASF CorporationInventors: Chacko Thankachan, Brian J. Betke, Michael C. Welch
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Patent number: 6028230Abstract: The amount of high molecular weight impurity present in a polyether polyol produced by alkoxylation of an active hydrogen-containing initiator using an epoxide such as propylene oxide and a substantially amorphous highly active double metal cyanide complex catalyst may be advantageously lowered by having a non-protic Lewis acid present during the epoxide polymerization. The use of halides such as zinc chloride and aluminum chloride is especially effective for such purposes. In a preferred embodiment, minor amounts of water are also present during polymerization. The higher purity polyether polyols thereby produced are particularly useful in the preparation of slab and molded polyurethane foams, which tend to collapse or become excessively tight when elevated levels of high molecular tail are present in the polyether polyol.Type: GrantFiled: June 5, 1998Date of Patent: February 22, 2000Assignee: Arco Chemical Technology, L.P.Inventors: Bi Le-Khac, Ulrich B. Holeschovsky, Michael A. Rueter
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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: 5962749Abstract: This invention relates to a process for the purification of polyether polyols. This process enables the removal of residual alkaline metal catalyst from produced polyether polyol. It comprises a) adding glycerine to a polyether polyol that contains Group IA alkaline metal catalyst to form a precipitate, and b) separating the precipitate formed in a) to provide a purified polyether polyol. The present invention also relates to the purified polyether polyol produced by this process, the precipitate produced by this process, and the use of the precipitate as an alkaline metal catalyst in a process for the production of polyether polyols.Type: GrantFiled: December 24, 1997Date of Patent: October 5, 1999Assignee: Bayer CorporationInventors: Harold R. Parsons, Donald C. Dunham, Steven L. Schilling, Keith J. Headley
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Patent number: 5962748Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step comprising reacting propylene oxide with an initiator having at least two hydroxyl groups in the presence of a basic catalyst, a second step of contacting the polyether product of the first step having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.Type: GrantFiled: October 23, 1997Date of Patent: October 5, 1999Assignee: Huntsman Petrochemical CorporationInventor: Timothy L. Lambert
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Patent number: 5942237Abstract: A novel type of formulation for the topical administration of antigens and/or vaccines to mammals via mucosal membranes comprising one or more adjuvants/vehicles selected from (a) polyoxyethylene sorbitan monoesters, (b) polyoxyethylene castor oil, (c) caprylic/capric acid glycerides and (d) gangliosides in an amount of 0.01 to 15% (v/v) calculated on the total volume of the preparation. This formulation enhances the immunological response n a mammal following mucosal administration, e.g. nasal, oral, rectal or vaginal application.Type: GrantFiled: October 6, 1995Date of Patent: August 24, 1999Assignee: Lyfjathroun H.F.Inventors: Sveinbjorn Gizurarson, Iver Heron
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Patent number: 5939591Abstract: Disclosed is an apparatus and process for producing a tripropylene glycol in which alkylene oxide, water, an acid catalyst and a dipropylene glycol are contacted together under conditions suitable to form the tripropylene glycol. Water is present in the reaction mixture in the range of about 1 to about 50 weight percent of the reaction mixture. The ratio of water to alkylene oxide is less than about 9. The tripropylene glycol thus produced exhibits a higher primary hydroxyl group content generally exceeding 36 percent. Such tripropylene glycols find utility in the production of acrylics. Also disclosed is a process for making esters from such glycols.Type: GrantFiled: December 1, 1997Date of Patent: August 17, 1999Assignee: The Dow Chemical CompanyInventors: Jeffrey David Birdwell, Micheal L. Chappell, Philip Jay Carlberg, Frank Harold Murphy, Robert Page Shirtum, Walter L. Wernli
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Patent number: 5912342Abstract: The invention relates to a compound of the formula (I) wherein whereinY is the fraction of a solid or soluble support, where Y may include a residue of a functional group having been attached to said support, said functional group having been hydroxy, amino, thio, epoxy or halogen,R.sup.1 is aryl, heteroaryl, alkyl chain or ring or ring system, which may include a heteroatom, or R.sup.1 is nothing, and R.sup.2 is vinyl;CH.sub.2 CH.sub.2 X, where X is halogen; orR.sup.3 C.dbd.CHR or R.sup.3 CH--CH.sub.2 R.sup.4 X, where R.sup.3 and R.sup.4 are the same or different and are alkyl, acyl, carbonyl, cyano or nitro groups and X is halogen.The invention also relates to a method for preparation of compound (I) and to its use as a substrate in the synthesis of tertiary amines. The invention still concerns a group of alpha-2-receptor active tetrahydroisoquinoline derivatives.Type: GrantFiled: August 12, 1997Date of Patent: June 15, 1999Inventors: Petri Heinonen, Harri Lonnberg, Victor Cockcroft
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Patent number: 5877245Abstract: The reaction product ofA) a linking compound of formula IR.sup.1 (X).sub.3 (I)wherein each X group is a halogen or one X group is a halogen and two X groups with 2 carbon atoms from the R.sup.1 group and an oxygen atom form an epoxy group, and R.sup.1 is an alkanetriyl group containing from 3 to 10 carbon atoms;B) a compound of formula IIR.sup.2 (OA).sub.n --OH (II)wherein R.sup.2 is an aliphatic group containing from 4 to 36 carbon atoms, n is a number of from 1 to 200, and each OA group is independently an ethyleneoxy, 1,2-propyleneoxy, or 1,2-butyleneoxy group; andC) a compound of formula IIIH--(OA).sub.m --OH (III)wherein OA is as defined above, and m is a number of from 1 to 500;processes for its preparation; and methods for its use as a thickener in aqueous compositions.Type: GrantFiled: August 15, 1997Date of Patent: March 2, 1999Assignee: Henkel CorporationInventors: Michael S. Wiggins, David I. Devore
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Patent number: 5798434Abstract: A monomer mixture having a hydroxyl value ranging from 0 to 134 KOH mg/g, obtainable by polymerizing a mixed raw material of an unsaturated compound selected from the group consisting of fatty acids each having one carboxyl group and one double bond in the molecule and having 11 to 22 carbon atoms and lower alkyl esters thereof with an unsaturated compound selected from the group consisting of fatty acids each having one carboxyl group and 2 to 4 double bonds in the molecule and having 11 to 22 carbon atoms and whose iodine value ranges from 30 to 130 g (iodine)/100 g to give dimers and trimers, then converting the carboxyl groups (or the lower alkyl ester group in case of the lower alkyl esters) present in the resulting dimers and trimers into hydroxyl groups through reduction to give a mixture substantially consisting of dimer diols and trimer triols, and then subjecting the mixture having a dimer diol/trimer triol weight ratio ranging from 30/70 to 99/1 to an esterification reaction with an .alpha., .beta.Type: GrantFiled: August 30, 1996Date of Patent: August 25, 1998Assignee: Lion CorporationInventors: Hitoshi Kigawa, Hiroshi Yamagishi, Noriko Suzuki, Yoshikazu Asao
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Patent number: 5780644Abstract: Branched, dendrimeric-type macromolecules composed essentially of a central nucleus and of a series of polyoxaalkyl chains that depart from said nucleus and spread into the surrounding space branching in a cascade fashion useful as carriers of drugs, contrast agents, etc.Type: GrantFiled: March 15, 1995Date of Patent: July 14, 1998Assignee: Dibra S.p.A.Inventors: Luigia Gozzini, Monica Muttoni, Christoph DeHaen
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Patent number: 5739208Abstract: A poly(ethylene glycol) derivative is disclosed that is activated with a sulfone moiety for selective attachment to thiol moieties on molecules and surfaces. The activated PEG is water soluble, hydrolytically stable for extended periods, and forms hydrolytically stable linkages with thiol moieties. The linkages generally are not reversible in reducing environments. The PEG derivative is useful for modifying the characteristics of substances including modifying biologically active molecules and surfaces for biocompatibility. Methods for synthesizing the active PEG and for preparing conjugates of the active PEG and other substances, including biologically active substances, are also disclosed.Type: GrantFiled: June 7, 1995Date of Patent: April 14, 1998Assignee: Shearwater Polymers, Inc.Inventor: J. Milton Harris
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Patent number: 5705667Abstract: The present invention concerns the use of dendrimeric-type branched macromolecules, comprising polyoxaalkylene chains, as catalysts or coadjuvants of phase transfer catalysis reactions.Type: GrantFiled: July 26, 1996Date of Patent: January 6, 1998Assignee: Dibra S.p.A.Inventors: Christoph De Haen, Luigia Gozzini, Monica Muttoni
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Patent number: 5698746Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step of contacting a polyether having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.Type: GrantFiled: November 4, 1996Date of Patent: December 16, 1997Assignee: Huntsman Petrochemical CorporationInventor: Timothy L. Lambert
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Patent number: 5696298Abstract: The present invention comprises novel preparations of polyoxypropylene/polyoxyethylene copolymers which retain the therapeutic activity of the commercial preparations, but are substantially free from the undesirable effects which are inherent in the prior art preparations. Because the preparations of polyoxypropylene/polyoxyethylene copolymers which comprise the present invention are a less polydisperse population of molecules than the prior art polyoxypropylene/polyoxyethylene copolymers, the biological activity of the copolymers is better defined and more predictable.Type: GrantFiled: June 2, 1995Date of Patent: December 9, 1997Assignee: CytRx CorporationInventors: R. Martin Emanuele, Robert L. Hunter, Paula H. Culbreth
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Patent number: 5672768Abstract: Low-odor, higher molecular weight polyether polyols are produced by purifying the polyether polyols at temperatures of 110.degree. to 150.degree. C. and pressures of 10 to 70 hPa with the addition of 5 to 30% by weight of water, wherein the water is passed in finely divided form, with a droplet diameter of about 5 to 100.mu., through the polyether polyols to be purified for a time of metered addition of 1 to 5 hours.Type: GrantFiled: January 8, 1997Date of Patent: September 30, 1997Assignee: Bayer AktiengesellschaftInventors: Pramod Gupta, Gundolf Jacobs, Joel Leuridan
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Patent number: 5672662Abstract: Active esters of PEG acids and related polymers are provided that have a single propionic or butanoic acid moiety and no other ester linkages. These polymer acids have a half life in water of from about 10 to 25 minutes. For example, alpha-methoxy, omega-propionic acid succinimidyl ester of PEG ("methoxy-PEG-SPA") has a nearly ideal reactivity with amino groups on proteins and other biologically active substances. The half life of methoxy-PEG-SPA is about 16.5 minutes in water. The invention also provides conjugates with proteins, enzymes, polypeptides, drugs, dyes, nucleosides, oligonucleotides, lipids, phospholipids, liposomes, and surfaces of solid materials that are compatible with living organisms, tissue, or fluid.Type: GrantFiled: October 2, 1995Date of Patent: September 30, 1997Assignee: Shearwater Polymers, Inc.Inventors: J. Milton Harris, Antoni Kozlowski
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Patent number: 5641853Abstract: A process for polymerizing oxepanes, dioxolanes, trioxanes, and tetrahydrofurans to their respective polymers by contacting them with a selected metal compound and an accelerator which is a selected vinyl ester or a selected phosphorous compound.Type: GrantFiled: February 28, 1996Date of Patent: June 24, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Neville Everton Drysdale
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Patent number: 5637673Abstract: Improved double metal cyanide (DMC) catalysts are disclosed. The catalysts comprise a DMC compound, an organic complexing agent, and from about 5 to about 80 wt. % of a polyether polyol that has tertiary hydroxyl groups. Compared with other DMC catalysts, those of the invention have excellent activity for epoxide polymerization, and they can be used to make polyols having very low unsaturation even at high epoxide polymerization temperatures.Type: GrantFiled: May 16, 1996Date of Patent: June 10, 1997Assignee: ARCO Chemical Technology, L.P.Inventor: Bi Le-Khac
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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: 5596059Abstract: Polyoxyalkylene polyether polyols suitable for preparation of flexible polyurethane foams are prepared by oxyalkylating an aqueous solution of one or more polyhydric, hydroxyl-functional solid initiators under conditions where both water as well as initiator are oxyalkylated. The polyols have calculated functionalities of between about 2.2 and 4.0 and hydroxyl numbers in the range of 10 to 180. The polyols may be used to prepare soft, high resiliency polyurethane flexible foams at low isocyanate indexes.Type: GrantFiled: July 26, 1995Date of Patent: January 21, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Stanley L. Hager, James E. Knight, Gregory F. Helma, Ben J. Argento
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Patent number: 5585458Abstract: A method for preparing polyether glycol is disclosed. An ester end-capped polyalkylene ether and an alcohol are subjected to alcoholysis at a temperature of 35.degree.-150.degree. C. and a pressure of 1-10 atm in the presence of a mixed metal oxide as a catalyst. The mixed metal oxide includes an alkaline earth metal oxide and at least one component selected from alumina, silica, and zinc oxide.Type: GrantFiled: June 27, 1995Date of Patent: December 17, 1996Assignee: Industrial Technology Research InstituteInventors: Wen-Fa Lin, Yu-Wen Chen, Jih-Chen Huang, Hsueh-Ying Chen
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Patent number: 5563221Abstract: A process for making high-primary, low-unsaturation polyols is disclosed. A polyol made by double metal cyanide (DMC) catalysis is blended with a polyol made by basic catalysis, and the polyol blend is reacted with ethylene oxide to produce an ethylene oxide-capped potyol. The process overcomes problems of the conventional recatalysis approach to making EO-capped polyols from DMC-catalyzed polyols.Type: GrantFiled: June 21, 1995Date of Patent: October 8, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: Jos e F. Pazos
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Patent number: 5488180Abstract: This invention relates to complex hydrophobe compounds and to alkoxylation products, i.e., condensation reaction products of alkylene oxides and complex hydrophobe compounds having at least one active hydrogen. This invention also relates to alkoxylation products that have beneficial, narrow molecular weight ranges.Type: GrantFiled: May 29, 1992Date of Patent: January 30, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard D. Jenkins, David R. Bassett, Danny E. Smith, John N. Argyropoulos, James E. Loftus, Gregory D. Shay
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Patent number: 5483008Abstract: The present invention relates to a bifunctional polyether having groups different from each other at both ends, with a polymerization degree of 5 to 10000 and consisting of repeating units each represented by the following formula (I): ##STR1## (wherein R.sub.1, represents a hydrogen atom, halogen atom, or a lower alkyl group optionally substituted by a halogen atom, and R.sub.1 in each repeating unit may be the same or different), as well as to a process for the preparation thereof and a polymerization initiator therefor. The process of production and polymerization initiator of the present invention enable 100% introduction of a primary amino group into one of the ends of polyether.Type: GrantFiled: February 5, 1993Date of Patent: January 9, 1996Assignee: Research Development Corporation of JapanInventors: Yasuhisa Sakurai, Teruo Okano, Masayuki Yokoyama, Kazunori Kataoka, Yukio Nagasaki, Nobuyuki Ohsako, Masao Kato
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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: 5446090Abstract: A poly(ethylene glycol) derivative is disclosed that is activated with a sulfone moiety for selective attachment to thiol moieties on molecules and surfaces. The activated PEG is water soluble, hydrolytically stable for extended periods, and forms hydrolytically stable linkages with thiol moieties. The linkages generally are not reversible in reducing environments. The PEG derivative is useful for modifying the characteristics of substances including modifying biologically active molecules and surfaces for biocompatibility. Methods for synthesizing the active PEG and for preparing conjugates of the active PEG and other substances, including biologically active substances, are also disclosed.Type: GrantFiled: November 12, 1993Date of Patent: August 29, 1995Assignee: Shearwater Polymers, Inc.Inventor: J. Milton Harris
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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: 5340916Abstract: The present invention relates to a process for the preparation of a hard foam containing urethane groups or urethane and isocyanurate groups by the polyisocyanate polyaddition process, by reactinga) a polyoxypropylene- or polyoxyethylene-polyoxypropylene-polyol containing secondary hydroxyl groups, having a functionality of from 3.5 to 4.3, a hydroxyl number of from 350 to 650 and a viscosity of from 500 to 2,500 mPa.multidot.s at 23.degree. C.Type: GrantFiled: October 26, 1992Date of Patent: August 23, 1994Assignee: BASF AktiengesellschaftInventors: Rolf Henn, Werner Hinz, Ludwig Schuster, Klaus Vorspohl
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Patent number: 5313000Abstract: This invention relates to the production of hydroxy-terminated polymers in the 2,000-20,000 MW range suitable for use as prepolymers in curing reactions with isocyanates to produce elastomers. The process involves the continuous addition over periods of 25-50 hours of an oxirane (monoepoxide) or a mixture of an oxirane and an oxetane to a reaction mixture, consisting of stoichiometric excesses of oxonium ion-forming catalyst such as BF.sub.3 -etherate and a diol initiator dissolved in an inert solvent. Under these conditions, chain extension of the diol occurs and the formation of cyclic oligomers and other impurities is minimised. The mole ratio of the initiator to catalyst is maintained at above 10:1 to suppress the formation of cationic terminal species on the growing polymer chain.Type: GrantFiled: January 27, 1992Date of Patent: May 17, 1994Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Britain and Northern IrelandInventor: Malcolm J. Stewart
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Patent number: 5294365Abstract: Hydroxypolyethers as low foam surfactants comprising a compound of the general formula ##STR1## wherein R.sup.1, R.sup.2 are the same or different and are a linear or branched C.sub.1 - to C.sub.18 -alkyl radical;n is a number of from 15 to 45; andm is a number of from 0 to 3.These compounds are useful in cleaning compositions and rinse aids, especially in automatic dishwashing machines.Type: GrantFiled: December 12, 1991Date of Patent: March 15, 1994Assignee: BASF CorporationInventors: Michael C. Welch, Jay G. Otten, Glenis R. Schenk
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Patent number: 5292965Abstract: Radiation curable compositions containing outstanding reactive diluents have been developed. The diluents are lower alkyl ether acrylates and methacrylates of particular alkoxylated and non-alkoxylated polyols.Examples are mono-methoxy trimethylolpropane diacrylate, mono-methoxy neopentyl glycol monoacrylate and mono-methoxy, ethoxylated neopentyl glycol monoacrylate having an average of about two moles of ethylene oxide.Type: GrantFiled: June 14, 1993Date of Patent: March 8, 1994Assignee: Diamond Shamrock Chemicals CompanyInventors: Francis A. Higbie, Robert A. LieBerman, Rose Ira M.
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Patent number: 5290912Abstract: The present invention has an object of producing a polyoxyalkylene compound by ring-opening polymerization of an alkylene oxide to a certain specific highly hydrophobic initiator. The present invention provides a process for producing a polyoxyalkylene compound, characterized in that the polyoxyalkylene compound is produced by ring-opening polymerization of an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from an organopolysiloxane compound having an active hydrogen-containing functional group to which an alkylene oxide is reactive, and a fluorine-containing compound having such an active hydrogen-containing functional group and a fluorinated hydrocarbon group.Type: GrantFiled: January 10, 1992Date of Patent: March 1, 1994Assignee: Asahi Glass Company Ltd.Inventors: Takashi Watabe, Hiromitsu Takeyasu, Shigeyuki Kozawa
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Patent number: 5254745Abstract: Polyoxyalkylene polyols initiated with melamine and coinitiated with toluene diamine and oxyalkylated with one or more alkylene oxides have relatively low viscosity and are suitable for preparing polyurethane foams.Type: GrantFiled: November 12, 1991Date of Patent: October 19, 1993Assignee: BASF CorporationInventor: Joachim Jahme
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Patent number: 5210322Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.Type: GrantFiled: September 20, 1990Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson
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Patent number: 5208379Abstract: Waste or scrap polyurethane may be conveniently and economically converted to useful active-hydrogen containing polyethers and polyamines by contacting the polyurethane with water, strong base, and an activating agent such as a quaternary ammonium compound containing at least 15 carbon atoms or an organic sulfonate containing at least 7 carbon atoms. The activating agent helps to accelerate the rate of base catalyzed hydrolysis.Type: GrantFiled: May 14, 1992Date of Patent: May 4, 1993Assignee: Arco Chemical Technology, L.P.Inventors: Lau S. Yang, Diane A. Macarevich
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Patent number: 5171747Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;D is an oxygen atom or a NOR group, wherein R.dbd.H or C.sub.1 -C.sub.4 alkyl;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group; andR'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain,useful as drugs.Type: GrantFiled: October 16, 1990Date of Patent: December 15, 1992Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5169989Abstract: An improved process for preparing a polyether polyol of reduced scorching properties comprising buffering of the alkaline polyether polyol before heating to remove water, and the use of said polyether polyol to prepare flexible foam slabstocks.Type: GrantFiled: March 1, 1991Date of Patent: December 8, 1992Assignee: Miles Inc.Inventors: Alfred L. Peterson, Mark S. Solomon, Kenneth E. Reed, Edward P. Squiller
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Patent number: 5160450Abstract: Novel surface active agents in the form of compounds of formulas (I) and (II) show higher surface activity. ##STR1## R.sup.1 and R.sup.2 are alkyl or alkenyl groups having 6 to 20 carbon atoms, Z is H, SO.sub.3 H, PO(OH).sub.2, CH.sub.2 COOH, (CH.sub.2).sub.2 SO.sub.3 H or a salt thereof, R.sup.3 and R.sup.4 are alkyl or alkenyl groups having 5 to 19 carbon atoms, R.sup.5 and R.sup.6 are alkyl groups having 1 to 4 carbon atoms, and n is a number of from 1 to 20.Type: GrantFiled: December 5, 1990Date of Patent: November 3, 1992Assignee: Lion CorporationInventors: Mitsuo Okahara, Araki Masuyama
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Patent number: 5135683Abstract: An improved process for the hydrolysis and purification of an alkoxylated polyol containing a ketal protective functionality is described. The process may be employed to prepare reduced calorie esterified alkoxylated polyol fat mimetics useful in cooking and in food compositions.Type: GrantFiled: March 28, 1991Date of Patent: August 4, 1992Assignees: Arco Chemical Technology, L.P., CPC International Inc.Inventor: Charles F. Cooper
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Patent number: 5124074Abstract: A novel anti-foaming agent is described which contains a compound produced by an addition reaction ofa mono-substituted poly(alkylene glycol) represented by the general formula:RO(AO).sub.x H (I)wherein R represents a monovalent hydrocarbon group having from 1 to 20 carbon atoms, AO represents a structural unit of an oxyalkylene chain, said structural unit having from 2 to 4 carbon atoms, and x represents a number of 1 to 80, witha polyepoxy compound represented by the general formula: ##STR1## wherein Q represents a residue of an organic compound containing in the molecule thereof 2 or more hydroxyl groups and either of a hydrocarbon chain having from 2 to 20 carbon atoms and an oxyalkylene chain having a polymerization degree of from 2 to 100, said residue having a valence of y and being formed by removing from 2 to 8 active hydrogen atoms from the organic compound, and y represents a number of 2 to 8.Type: GrantFiled: May 20, 1991Date of Patent: June 23, 1992Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Yoshitaka Uchiyama, Harumi Suzuki
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Patent number: 5104987Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5053554Abstract: Radiation curable compositions containing outstanding reactive diluents have been developed. The diluents are lower alkyl ether acrylates and methacrylates of particular alkoxylated and non-alkoxylated polyols.Examples are mono-methoxy trimethylolpropane diacrylate, mono-methoxy neopentyl glycol monoacrylate and mono-methoxy, ethoxylated neopentyl glycol monoacrylate having an average of about two moles of ethylene oxide.Type: GrantFiled: January 30, 1990Date of Patent: October 1, 1991Assignee: Diamond Shamrock Chemical CompanyInventors: Francis A. Higbie, Robert A. LieBerman, Ira M. Rose
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Patent number: 5025094Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zirconium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.Type: GrantFiled: June 13, 1989Date of Patent: June 18, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 4963535Abstract: Cosmetic compositions for cleaning hair, the skin or for removing make-up from the face or from the eyes, containing (a) a foaming surface-active agent, (b) an aqueous, hydroalcoholic or oily carrier and (c) a nonfoaming, nonionic product, poorly soluble in water, of general formula (I):R--O--[C.sub.2 H.sub.3 --CH.sub.2 R.sub.1 --O].sub.p [C.sub.2 H.sub.3 O--CH.sub.2 OH].sub.n H (I)in which R denotes a C.sub.8 -C.sub.20 alkyl radical, R.sub.1 denotes a C.sub.7 -C.sub.17 alkyl radical or an alkoxy radical containing from 8 to 20 carbon atoms, R+R.sub.1 containing from 21 to 31 carbon atoms and preferably from 23 to 27, p denotes the exact value of 1 or a statistical mean value of between 1 and 2, and n denotes a statistical mean value of between 2 and 10 and preferably between 2.5 and 7.The presence of the component (c) improves the compatibility of the foaming surface-active agents (a) with the skin and the mucosa.Type: GrantFiled: February 2, 1988Date of Patent: October 16, 1990Assignee: L'OrealInventors: Henri Sebag, Guy Vanlerberghe
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Patent number: 4960953Abstract: A process for the preparation of polyglycerols which are low in cyclic components comprises reacting glycerol or diglycerol or a higher polyglycerol with epichlorohydrin at elevated temperatures; adding base corresponding to the organically bound chlorine content of the reaction mixture, at a temperature of 50.degree.-120.degree. C., to the unseparated reaction mixture obtained; desalting the resultant reaction mixture and recovering glycerol, diglycerol and higher polyglycerols by fractional distillation.Type: GrantFiled: March 24, 1989Date of Patent: October 2, 1990Assignee: Deutsche Solvay-Werke GmbHInventors: Gerald Jakobson, Werner Siemanowski
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Patent number: 4943664Abstract: What is provided herein are new and useful surfactants characterized by having a large number of hydroxyl hydrophilic groups therein with the formula: ##STR1## where R is a long chain alkyl group,Z is O or --NH, andn=1-4.Type: GrantFiled: September 22, 1989Date of Patent: July 24, 1990Assignee: GAF Chemicals CorporationInventors: Lowell R. Anderson, Mohamed M. Hashem, Robert B. Login
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Patent number: 4886917Abstract: Narrow, balanced alkoxylation product mixture distributions having at least one alkoxylation product constituting more than 20 weight percent of the mixture can be provided by modified, calcium-containing catalysts. Catalysts for alkoxylation processes can be produced from lime and can, with modification, be used to make the narrow, balanced alkoxylation product mixture distribution.Type: GrantFiled: October 6, 1986Date of Patent: December 12, 1989Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Robert J. Knopf, Louis F. Theiling, Jr.
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Patent number: RE33307Abstract: Novel substituted cis-1,2-dihydroxy-cyclohexa-3,5-diene compounds, useful as intermediates in the production of phenols and catechols for use as intermediates in the production of drugs, herbicides, insecticides and as chiral synthons, in particular cis-1,2-dihydroxy-3-trifluoromethyl-cyclohexa-3,5-diene. A process for producing the novel compounds is also claimed.Type: GrantFiled: December 30, 1988Date of Patent: August 21, 1990Assignee: Imperial Chemical Industries PLCInventors: Stephen C. Taylor, Michael D. Turnbull