Ethers Patents (Class 536/120)
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Patent number: 5906924Abstract: High quality trehalose derivatives are readily prepared in a considerably high yield by reacting anhydrous trehalose with reactive reagents under anhydrous conditions. The trehalose derivatives can be used in a variety of fields in the production, the chemical synthesis, and the enzymatic synthesis of foods, cosmetics, pharmaceuticals, detergents and chemicals as surfactants, humectants, skin-beautifying agents, antitumor agents, and intermediates for chemical and enzymatic syntheses.Type: GrantFiled: November 28, 1995Date of Patent: May 25, 1999Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kaguku KenkyujoInventors: Takahiko Mandai, Takashi Shibuya, Toshiyuki Sugimoto
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Patent number: 5900478Abstract: Reaction at the interface of an organic solution containing an acidic reactant and an aqueous alkaline solution containing nonreducing carbohydrates such as sucrose, sugar alcohols, cyclodextrins, and polysaccharides imparts a specificity to the reaction for one or more of the primary alcohol groups of the carbohydrate reactant. The resulting activated, nonreducing carbohydrate intermediate can then be converted to a series of substantially pure, low molecular weight reaction products, including a sucrose trimer and dianhydrosucrose, and to a series of substantially pure, higher molecular weight reaction products, including 6-O-sucro cyclodextrins and poly-6-O-sucro amylose.Type: GrantFiled: June 20, 1997Date of Patent: May 4, 1999Assignee: Iowa State University Research Foundation, Inc.Inventors: John F. Robyt, Rupendra Mukerjea
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Patent number: 5891854Abstract: Cosmetic ceutical formulations characterized by an effective, content of pharmaceutically and/or cosmetically unobjectionable hexosyl glycerides and/or (hexosyl)hexosyl glycerides.Type: GrantFiled: October 24, 1996Date of Patent: April 6, 1999Assignee: Beiersdorf AGInventors: Joachim Thiem, Oliver Scheel, Gunther Schneider
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Patent number: 5886161Abstract: The process for producing an alkylglycoside, wherein the amount of coarse sugar particles in alkylglycoside can be reduced without reducing reaction yield, is provided.The process for producing an alkylglycoside comprises,a) mixing a hydrated solid sugar with a higher alcohol;b) dehydrating the mixture at a reduced pressure at a temperature of lower than a melting point of the hydrated solid sugar until a water content of the solid sugar becomes not more than 0.5% by weight;c) heating the mixture to 90.degree.-140.degree. C. so that the proportion of particles having a particle diameter of 0.3 mm or more may be not more than 0.1% by weight of the solid sugar in the mixture at the end of this step;d) reacting the mixture with an acid catalyst added thereto at a temperature of 90.degree.-140.degree. C. at a pressure of 5-100 mmHg; ande) neutralizing the acid catalyst contained in the product mixture with an alkali after the reaction has been completed.Type: GrantFiled: May 22, 1998Date of Patent: March 23, 1999Assignee: Kao CorporationInventors: Hiroshi Oka, Kenichi Tachi
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Patent number: 5872245Abstract: This present invention pertains to a process for the synthesis of sucrose fatty acid esters by reacting sucrose and a purified specific fatty acid ester under substantially solvent free conditions in the presence of a transesterification stationary catalyst and mechanical emulsification. The process is continuous, yielding selected individual products of separated simple sucrose fatty acid esters of mono-, di-, tri- and polyesters while recycling the unwanted ester fractions, the unreacted sucrose and fatty acid ester.Type: GrantFiled: September 30, 1992Date of Patent: February 16, 1999Assignee: Optima Technologies GroupInventor: Donald C. Wilson
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Patent number: 5861048Abstract: Phosphorylated saccharide of the present invention includes at least one phosphate group in its molecule, selected from the group consisting of glucan, mannan, dextran, agar, cyclodextrin, fucoidan, gellan gum, Locust bean gum, guar gum, tamarind gum, and xanthan gum.Type: GrantFiled: August 11, 1995Date of Patent: January 19, 1999Assignee: Ezaki Glico Co., Ltd.Inventors: Hiroshi Kamasaka, Shigetaka Okada, Kaname Kusaka, Kazuya Yamamoto, Kenji Yoshikawa
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Patent number: 5854030Abstract: Sugar-containing poly(acrylate)-based hydrogels and methods of preparing these hydrogels are disclosed. Poly(sugar acrylate)s are chemeoenzymatically prepared and crosslinked to form hydrogels, which are water absorbant.Type: GrantFiled: December 11, 1995Date of Patent: December 29, 1998Assignee: University of Iowa Research FoundationInventors: Jonathan S. Dordick, David G. Rethwisch, Damodar R. Patil, Brett D. Martin, Robert J. Linhardt
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Patent number: 5843907Abstract: 2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-gluco-pyranosyl-L-acorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.Type: GrantFiled: February 27, 1995Date of Patent: December 1, 1998Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Shuzo Sakai, Masaru Yoneyama, Toshio Miyake
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Patent number: 5844058Abstract: A new family of polysaccharide graft polymers are provided as corrosion resistant coatings having antimicrobial properties which are useful on light metals such as aluminum, magnesium, zinc, steel and their alloys. Methods of making the polysaccharide graft polymers are also included. The methods of making the polysaccharide graft polymers involve reacting a polysaccharide source with an antimicrobial agent under conditions of hydrolysis-condensation.Type: GrantFiled: December 17, 1996Date of Patent: December 1, 1998Assignee: Brookhaven Science AssociatesInventor: Toshifumi Sugama
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Patent number: 5840703Abstract: A reaction mixture for manufacturing polyol fatty acid polyesters comprises a polyol, a fatty acid lower alkyl ester, a base initiator and a phase transfer catalyst. The phase transfer catalyst can be a quaternary ammonium compound, a crown ether, a polyethylene glycol, a polyethylene glycol ether, a polyethylene glycol ester or mixtures thereof. The process of making polyol fatty acid polyesters is carried out at low temperatures and essentially in the absence of a solvent or emulsifier. The polyol fatty acid polyester product stream produced by the foregoing process and reaction mixture has a lower concentration of reaction by-products such as di-fatty ketones and beta-ketoesters and of caramelized by-product which results from the breakdown of the polyol reactant.Type: GrantFiled: November 15, 1996Date of Patent: November 24, 1998Inventors: Patrick J. Corrigan, John K. Howie
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Patent number: 5830920Abstract: Compounds of the formula ##STR1## wherein n.sup.1 -n.sup.9 are each independently 0 or 1;m.sup.1 -m.sup.9 are each independently 0 or 1, but with the proviso that at least one of m.sup.1, m.sup.2 and m.sup.3, at least one of m.sup.4, m.sup.5 and m.sup.6 and, when present, at least one of m.sup.7, m.sup.8 and m.sup.9 is 1; and whereinX.sup.1 -X.sup.18 each independently is --O--, --CONR.sup.1,--NR.sup.1 CO-- or --NR.sup.1 --;R.sup.1 is hydrogen or lower alkyl;W is a benzene or s-triazine;Y.sup.1 -Y.sup.9 each independently is an aromatic ring systems;A.sup.1 -A.sup.3 each independently is a residue of a sugar alcohol devoid of the 1-hydroxy group or a derivative thereof, a residue of a sugar acid devoid of the 1-carboxy group or a derivative thereof or tris-(hydroxymethyl)-methyl;D is the di-residue of a sugar alcohol devoid of 2 hydroxy groups or a derivative thereof or the di-residue of a sugar dicarboxylic acid devoid of 2 carboxy group or a derivative thereof;Q.sup.1 -Q.sup.3 and Z.sup.Type: GrantFiled: April 26, 1996Date of Patent: November 3, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Alexander Chucholowski, Jurgen Fingerle, Niggi Iberg, Hans Peter Marki, Rita Muller, Michael Pech, Marianne Rouge, Gerard Schmid, Thomas Tschopp, Hans Peter Wessel
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Patent number: 5831080Abstract: The present invention relates to organosilicon compounds containing glycoside radicals, having units of the formula ##STR1## in which R is identical or different and represents a hydrogen atom or an organic radical,a is 0, 1, 2 or 3,b is 0, 1, 2 or 3 andR.sup.1 can be identical or different and represents a radical of the formulaZ--(R.sup.2 O).sub.c --R.sup.3 -- (II)in whichZ represents a glycoside radical which is built up from 1 to 10 monosaccharide units,R.sup.2 can be identical or different and represents an alkylene radical,c is 0 or a number from 1 to 20, andR.sup.3 represents an alkylene radical, with the proviso that the sum of a and b is less than or equal to 3 and the organosilicon compound comprising units of the formula (I) contains at least one radical R.sup.1 per molecule.Type: GrantFiled: April 22, 1996Date of Patent: November 3, 1998Assignee: Wacker-Chemie GmbHInventors: Johann Sejpka, Franz Wimmer
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Patent number: 5830872Abstract: Esters associating phenylacetic, 3-phenylpropionic, 4-phenylbutyric and n-butyric acids with Su(OH).sub.n monosaccharides or sugar alcohols, of general formula (I), in which the Su(OH).sub.n precursor is a monosaccharide or sugar alcohol, selected so that its structure or that of its derivatives ensures that internal interesterification does not take place either because the ester based on the general formula does not have a free hydroxyl grouping, or because with regard to the ester grouping, the free hydroxyl groupings are remotely located and/or badly aligned and/or bonded to a secondary carbon atom, and in which the Su(OH).sub.n monosaccharide or sugar alcohol is preferably D-mannose carrying the ester grouping on the anomeric carbon atom or else is a pentitol, for example, xylitol carrying the ester grouping on the C-1 primary carbon atom. These novel esters are useful as drugs, in particular in the treatment of haemoglobin diseases and premalignant or malignant tumours.Type: GrantFiled: March 11, 1997Date of Patent: November 3, 1998Assignee: L'Associazione di volontariato "Pro La Fondazione Futuro Senza Thalassemia"Inventors: Pierre Jean Baldwin, Olivier Claude Eric Douillet, Philippe Rene Michel Pouillart, Gino Lino Ronco, Pierre Joseph Villa
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Patent number: 5795978Abstract: Emulsifiers particularly suitable for the production of storable, high-viscosity and sensorially light o/w emulsions contain from about 43% to about 99% by weight of an alkyl and/or alkenyl oligoglycoside and from about 1% to about 57% by weight of a fatty alcohol.Type: GrantFiled: November 14, 1996Date of Patent: August 18, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Achim Ansmann, Rolf Kawa, Michael Nitsche, Helga Gondek
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Patent number: 5792842Abstract: A ganglioside GM3 derivative having a fluorine atom at the 9-position of sialic acid represented by the formula: ##STR1## wherein R is an aliphatic lower acyl group, R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 to R.sup.5 represent independently of one another a hydrogen atom, an aliphatic lower acyl group or an aromatic acyl group, R.sup.11 is an straight or branched, saturated or unsaturated aliphatic hydrocarbon group having 1 to 30 carbon atoms, and n is an integer of 0 to 20, provided that when R.sup.1 is a hydrogen atom, R.sup.2 to R.sup.5 are hydrogen atoms, or when R.sup.1 is a lower alkyl group, R.sup.2 to R.sup.5 are each an aliphatic lower acyl group or an aromatic acyl group, and intermediates therefor. This compound is useful as an agent for preventing infection of the influenza virus, an agent for preventing proliferation and metastasis of the cancer cells, etc.Type: GrantFiled: April 16, 1996Date of Patent: August 11, 1998Assignee: Daikin Industries Ltd.Inventors: Takao Iida, Yutaka Ohira
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Patent number: 5792843Abstract: Alkyl and/or alkenyl oligoglucosides can be produced at high reaction rates by a process in which glucose having a particle size distribution of at least 80% in the 20 to 300 .mu.m range is subjected to acidic acetalization with fatty alcohols. Products having a high percentage content of mono-glucosides are obtained.Type: GrantFiled: January 22, 1996Date of Patent: August 11, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Paul Schulz, Rainer Eskuchen
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Patent number: 5792858Abstract: Novel derivatives of lysophingolipids free from sialic acids which are N-acyllysosphingolipids having one of the two formulae: ##STR1## in which -A- stands for the group --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --, n.sub.1 is a whole number of between 6 and 18, n.sub.2 is a whole number of between 11 and 15, X is a hydrogen atom or the residue of a monosaccharide or a disaccharide or phosphorylcholine and R represents an alkyl radical derived from a saturated or unsaturated aliphatic carboxylic acid having from 2 to 24 carbon atoms substituted by one or more polar groups. The lysosphingolipid derivatives of the invention exhibit an inhibiting action on protein-kinase C activation and, thus, can be utilized in therapies for various pathologies of the nervous system.Type: GrantFiled: April 5, 1996Date of Patent: August 11, 1998Assignee: FIDIA S.p.A.Inventors: Francesco Della Valle, Aurelio Romeo
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Patent number: 5789393Abstract: Water-soluble, high-viscosity grade cellulose ether compositions are useful for the reduction of serum lipid levels, particularly total serum cholesterol, serum triglycerides, and low-density lipoprotein (LDL) levels and/or attenuate the postprandial rise of blood glucose levels in animals. The pharmaceutical uses of compositions for reducing cholesterol levels additionally include the treatment of diabetes and/or hypercholesterolemia, with avoidance of many of the undesirable side effects associated with other forms of treatment. The composition may be in the form of a prehydrated ingestible composition, such as a gelatin, or a comestible, such as a cookie. In addition, the compositions of the present invention are palatable to the patient, thereby enhancing patient compliance with the regimen.Type: GrantFiled: June 7, 1995Date of Patent: August 4, 1998Assignees: The Board of Regents of the University of Michgan, The Dow Chemical CompanyInventors: Jennifer B. Dressman, Christos Reppas, Stephen W. Tobey, Cynthia W. Sowle
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Patent number: 5783692Abstract: This invention relates to novel alkylpolysaccharide dertivatives including their salts and compositions comprising said alkyl polysaccharides. The alkyl polysaccharide derivatives are of the formula (I): R.sup.1 --(OG).sub.n (X).sub.m, where R.sup.1 is hydrogen or a hydrophobic moiety; G is a saccahride residue; and X is a succinic anhydride residue; and n and m are independently chosen from an average value which is between 1 and 200.Type: GrantFiled: August 21, 1997Date of Patent: July 21, 1998Assignee: ICI Australia Operations Proprietary LimitedInventors: Andrew Francis Kirby, Keith Moody
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Patent number: 5780618Abstract: A method for making an oxidized cellulose product from a cellulose material is disclosed. The method involves oxidizing a cellulose material into an oxidized cellulose product, comprising treating the cellulose material with a hypochlorite solution having an active chlorine content of between about 4 and about 6%, at a pH exceeding 9.5 and at a temperature, and for a time, effective to convert the cellulose material into the oxidized cell product; filtering the oxidized cellulose product; and washing the oxidized cell product with an antichlor agent such as sodium thiosulfate to remove chlorine and to raise the oxidized cellulose product to a neutral pH.The oxidized cellulose product may be used to form films, dispersions, gels, as carriers, for pharmaceuticals, cosmetics and other products.Type: GrantFiled: April 28, 1995Date of Patent: July 14, 1998Assignee: Biocontrol IncorporatedInventors: Gilbert S. Banker, Vijay Kumar
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Patent number: 5777102Abstract: A method of producing a carrageenan-containing product comprising reacting a carrageenan-containing seaweed starting material in a substantially homogenous mixture of a solvent in which carrageenan is substantially insoluble, and an alkaline aqueous phase, ans subjecting the reacted and washed seaweed to shear stress, and a carrageenan-containing product obtainable by the method.Type: GrantFiled: June 28, 1995Date of Patent: July 7, 1998Assignee: Grindsted Products A/S (Danisco)Inventor: Peter Fromholt Larsen
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Patent number: 5767255Abstract: The present invention relates to glucose- and sophorose-lipids of the formula I ##STR1## in which R.sup.4 is --OH or a group of the formula II, ##STR2## n is an integer from 2 to 26, R.sup.1 and R.sup.2 are, independently of one another, H or ##STR3## R.sup.3 is H or --OH in the case where R.sup.4 is --OH, and is H or --OH or a group of the formula III, ##STR4## in the case where R.sup.4 is a group of the formula II, to a process for obtaining them by fermentation, and to their use as surfactants.Type: GrantFiled: May 20, 1996Date of Patent: June 16, 1998Assignee: Hoechst AktiengesellschaftInventors: Dieter Wullbrandt, Carlo Giani, Andreas Brakemeier, Siegmund Lang, Fritz Wagner
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Patent number: 5763586Abstract: The extraction of proteins from selected naturally occurring membranes without any harmful, adverse, or other deleterious effect(s). In one preferred embodiment the detergent is prepared from the reaction of a cycloalkyl aliphatic alcohol and a saccharide.Type: GrantFiled: November 12, 1996Date of Patent: June 9, 1998Assignee: Anatrace, Inc.Inventor: Don N. Gray
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Patent number: 5760200Abstract: A water insoluble, biocompatible composition that is formed by a method which combines, in an aqueous mixture, a polyanionic polysaccharide, a nucleophile, and an activating agent, under conditions sufficient to form the composition. Also, a water insoluble, biocompatible composition that is formed by a method which combines, in an aqueous mixture, a polyanionic polysaccharide, a modifying compound, a nucleophile and an activating agent under conditions sufficient to form the composition.Type: GrantFiled: January 25, 1995Date of Patent: June 2, 1998Assignee: Genzyme CorporationInventors: Robert J. Miller, Xuejian Xu
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Patent number: 5756716Abstract: Disclosed is a process for manufacturing an sugar ester product of a sugar and a fatty acid. First, a fatty acid and methyl or ethyl alcohol is reacted in the presence of sulfuric acid catalyst to produce a fatty acid ester and water. The sulfuric acid catalyst is neutralized with a metal carbonate to make a metal sulfate, with the fatty acid ester being separated from the metal sulfate, the alcohol and the water. The recovered fatty acid ester is reacted in the presence of a metal carbonate catalyst with sugar dissolved in dimethyl sulfoxide to produce the sugar ester product and alcohol. The dimethyl sulfoxide is separated from the reaction mixture by vacuum distillation, and then water is added to emulsify the sugar ester product and unreacted fatty acid ester. The unreacted sugar and the metal carbonate is dissolved in the water.Type: GrantFiled: June 7, 1995Date of Patent: May 26, 1998Assignee: Kimball Chase Tech. Ltd.Inventors: William A. Farone, Robert W. Serfass
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Patent number: 5756720Abstract: Nonionic and cationic derivatized guar gum which demonstrates greater than 75% light transmission at a wavelength of from about 500-600 nanometers when dispersed in water in the amount of 0.5 parts per 100 parts water and the process for producing such guar gum is disclosed. The compositions are particularly useful for producing products having utility in personal care and industrial cleaning products.Type: GrantFiled: October 25, 1996Date of Patent: May 26, 1998Assignee: Rhodia Inc.Inventor: Manjit Singh Chowdhary
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Patent number: 5756718Abstract: Disclosed are lipid A analogs useful for the treatment of septic shock and LPS-mediated activation of viral infection.Type: GrantFiled: June 7, 1995Date of Patent: May 26, 1998Assignee: Eisai Co., Ltd.Inventors: William J. Christ, Lynn D. Hawkins, Tsutomu Kawata, Daniel P. Rossignol, Seiichi Kobayashi, Osamu Asano
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Patent number: 5746933Abstract: A lubricating oil for refrigerating machines comprises polyoxyalkylene compounds represented by the formula (I): ##STR1## Wherein A is a residue obtained from a compound which has both a heterocyclic ring having an ether linkage therein and hydroxyl groups by eliminating the hydroxyl groups from the compound; R.sup.1 and R.sup.2 are each an alkylene group; R.sup.3 is an alkyl group; R.sup.4 is hydrogen atom or an alkyl group; a and b are each a positive integer and l, m, and n are each an integer of 0 or more; and a.multidot.1+b.multidot.m=2 to 100 and l+m+n=2 to 20; further,the polyoxyalkylene compounds have a hydroxyl value ranging from 0 to 30.0 mgKOH/g and satisfies the following formula (1)0.5<p/(p+q)<1.0 (1)wherein p is the number of butylene groups represented by R.sup.1 and R.sup.2, and q is the number of all alkylene groups excluding the butylene groups.Type: GrantFiled: November 3, 1995Date of Patent: May 5, 1998Assignee: Nippon Oil Co., Ltd.Inventors: Noboru Ishida, Umekichi Sasaki, Katsuya Takigawa, Satoshi Suda
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Patent number: 5739301Abstract: 1-(2'-hydroxy- and 2'-sulfatoalkyl)glycosides of formula I ##STR1## where X is a hydroxyl or a sulfato group of the formula OSO.sub.3 M, whereM is hydrogen, an alkali metal or an ammonium cation which can be substituted by organic radicals,R is a C.sub.6 - to C.sub.30 -alkyl or alkylene radical andGly is the radical of a monosaccharide acetalized in the 1-position by the group designated above,are described.The glycosides I are suitable as surfactants or emulsifiers in detergents, cleaning compositions or personal hygiene compositions.Type: GrantFiled: August 15, 1996Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Alfred Oftring, Beate Strecker, Gunter Oetter, Richard Schmidt, Wolfgang Klotz, Hendrik Wulff
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Patent number: 5739300Abstract: The invention relates to conjugates which consist of mono- or polycarboxylated piperidine or pyrrolidine derivatives and pyranoses, furanoses or polyalcohols linked via a chain or a cyclic system. The carboxyl groups of the piperidine derivatives can either be located directly on the ring or linked to the ring via a short chain. The invention additionally relates to the preparation of these compounds and to their use for the production of pharmaceuticals and diagnostics.Type: GrantFiled: October 4, 1996Date of Patent: April 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Alexander Toepfer, Gerhard Kretzschmar, Bernward Scholkens, Peter Klemm, Christoph Huls, Dirk Seiffge
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Patent number: 5734029Abstract: An improved alkylpolyglycoside surfactant composition, and method of preparing same, by selecting an average chain length of the alkyl moiety of the composition and mixing two or more of at least binary components having an average alkyl chain lengths such that when mixed, the amounts thereof are effective to provide the predetermined, selected average alkyl moiety of the surfactant composition. The improved alkylpolyglycoside composition is used in a variety of end-use applications, including hard surface cleaners, laundry detergents, and personal care products, such as shampoos, soaps, facial cleansers, foam baths, toothpaste, mouthwashes, antiperspirants and the like.Type: GrantFiled: June 7, 1995Date of Patent: March 31, 1998Assignee: Henkel CorporationInventors: Harald P. Wulff, Paul A. Siracusa, Patricia E. Bator, Barry A. Salka, Michael W. Counts, Robert A. Aleksejczyk
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Patent number: 5726303Abstract: The invention relates to the new product lactitol monohydrate and to a method for the production of crystalline lactitol. The crystalline lactitol monohydrate can be obtained bij seeding an aqueous lactitol solution of a special concentration under special conditions causing the lactitol monohydrate to crystallize and recovering the product. From the mother liquor a further amount of lactitol dihydrate can be recovered. Crystalline lactitol dihydrate can be obtained using different special conditions. Lactitolmonohydrate can further be obtained by mixing one part bij weight of an aqueous lactitol solution of a suited concentration with 1 tot 3 parts bij weight of methanol or ethanol and cooling the mixture to 15.degree. tot 25.degree. C.Type: GrantFiled: October 4, 1991Date of Patent: March 10, 1998Assignee: C.V. Chemie Combinatie Amsterdam C.C.A.Inventors: Christiaan F. Wijnman, John A. van Velthuijsen, Hendrik van den Berg
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Patent number: 5723590Abstract: The invention relates to compounds of formula (I) herein which are reaction products of alkylglycosides with aldehydes and/or diacetals of short-chain alcohols and aldehydes, the acetals obtained being alkoxylated. The invention further relates to a process for producing the above-mentioned compounds and to the use of these compounds for preparing surfactants, especially for industrial detergents and cleaners.Type: GrantFiled: May 23, 1996Date of Patent: March 3, 1998Assignee: Huels AktiengesellschaftInventors: Herbert Koch, Wulf Ruback, Wolfgang Schroeder
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Patent number: 5717081Abstract: In a process for producing an alkylglycoside by glycosidation of a saccharide or reglycosidation of a lower alkylglycoside in the presence of an acidic catalyst, the water of the reactor is removed by pervaporation. Also an apparatus for carrying out the reaction has been described.Type: GrantFiled: February 14, 1996Date of Patent: February 10, 1998Assignee: Unichema Chemie B.V.Inventor: Johannes Groen
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Synthesis of the breast tumor-associated antigen defined by monoclonalantibody MBRL and uses thereof
Patent number: 5708163Abstract: The present invention provides a process for synthesizing a compound having the structure: ##STR1## wherein R is H, as well as related oligosaccharides useful as a vaccine for inducing antibodies to human breast cancer cells in an adjuvant therapy therefor.Type: GrantFiled: April 28, 1995Date of Patent: January 13, 1998Assignee: Sloan-Kettering Institute of Cancer ResearchInventors: Samuel J. Danishefsky, Mark T. Bilodeau, Shuang Hua Hu, Tae Kyo Park, John T. Randolph, In Jong Kim, Philip O. Livingston -
Patent number: 5698684Abstract: In the acid-catalyzed production of alkyl glycosides, the molar quantity of catalyst used can be clearly reduced in all processes of industrial interest by using sulfosuccinic acid as catalyst as opposed to conventional catalysts, such as sulfuric acid or p-toluene sulfonic acid. The end reaction products are lighter in color and less clouded than alkyl glycosides obtained with conventional catalysts. Sulfosuccinic acid is readily biodegradable.Type: GrantFiled: February 24, 1992Date of Patent: December 16, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karlheinz Hill, Manfred Weuthen, Hans-Peter Koehler
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Patent number: 5681948Abstract: A two-stage method for the preparation of polyol fatty acid polyesters is provided. The resulting polyol fatty acid polyesters are very lightly colored (i.e., colorless to slightly yellow) and have a high degree of substitution with fatty acid groups. The first stage of this two-stage method is a solvent-based esterification reaction; the second stage is an essentially solvent-free esterification reaction. In the first stage, a polyol in a solvent (e.g., sucrose in dimethylsulfoxide)) is reacted with fatty acid lower alkyl esters at relatively low temperatures using an alkaline salt catalyst. After the desired degree of esterification is obtained, the resulting partially-esterified polyol fatty acid polyesters and the solvent-containing phase are separated.Type: GrantFiled: March 6, 1995Date of Patent: October 28, 1997Assignee: Kraft Foods, Inc.Inventors: Mark Stuart Miller, Leslie George West, Robert Charles Dinwoodie, Richard S. Silver
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Patent number: 5668275Abstract: The application relates to a novel process for bleaching alkyl polyglycosides having C.sub.8 - to C.sub.20 -alkyl groups in aqueous solution using peroxy compounds. The bleaching is carried out in a tubular reactor.Type: GrantFiled: September 7, 1995Date of Patent: September 16, 1997Assignee: Huels AktiengesellschaftInventors: Jurgen Grutzke, Stefan Schmidt
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Patent number: 5668274Abstract: The invention relates to sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type, of which N-sulfate, N-acetate, and hydroxy groups, are replaced by alkoxy, aryloxy, aralkoxy, or O-sulfate groups. The compounds have antithrombotic and smooth muscle cell proliferation inhibiting activities.Type: GrantFiled: May 23, 1996Date of Patent: September 16, 1997Assignee: Akzo Nobel N.V.Inventors: Maurice Petitou, Constant Adriaan Anton van Boeckel
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Patent number: 5661130Abstract: The present invention relates to a method of increasing the absorption of a compound via the ocular, nasal, nasolacrimal or inhalation route into the circulatory system of a patient. In particular, a method comprising administering with the compound an absorption enhancer comprising a nontoxic, nonionic alkyl glycoside is provided. Additionally provided are methods of raising or lowering the blood glucose level by administering glucagon or insulin, respectively, with such absorption enhancers. Finally, compositions for raising or lowering the blood glucose level are provided.Type: GrantFiled: June 24, 1993Date of Patent: August 26, 1997Assignee: The UAB Research FoundationInventors: Elias Meezan, Dennis J. Pillion
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Patent number: 5659021Abstract: Enantiomerically pure glycerol derivatives, e.g. S-1,2-O-isopropylidene, S-1,2-O-benzylidene, and R-1,2-O-dibenzyl glycerol, have been prepared from 1,2R-O-protected erythritols in high yields. The latter compounds are easily obtained from erythorbic acid and are useful building blocks in the synthesis of a host of optically active compounds having biological activity.Type: GrantFiled: July 25, 1994Date of Patent: August 19, 1997Assignee: The Board of Governors for Higher Education, State of Rhode Island and Providence PlantationsInventor: Elie Abushanab
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Patent number: 5658880Abstract: Compounds that exhibit selectin binding activity are described and have the following structural formula: ##STR1## where W is selected from a group including structures a-d below ##STR2## wherein p is an integer of from 0-2, q is an integer of from 0-3, and r is an integer of from 0-5;A is selected from the group consisting of .alpha. and .beta. forms of sialic acid, Kemp's acid, quinic acid, R and S forms of mandelic acid, R and S forms of glyceric acid, R and S forms of lactic acid, propionic and acetic acid, and esters and amides thereof, --SO.sub.3, sulfonate, --PO.sub.3, phosphonate, trifluoromethyl, diazine and triazine;B is selected from a group consisting of .alpha. and .beta. forms of fucose, arabinose and esters and substituted forms thereof wherein one or more of the OH groups is independently substituted with F, N.sub.3, NHAc, NHCOCF.sub.3. The remaining variable are described in the specification.Type: GrantFiled: August 12, 1994Date of Patent: August 19, 1997Assignee: Glycomed IncorporatedInventors: Falguni Dasgupta, John H. Musser, Daniel E. Levy, Peng Cho Tang
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Patent number: 5646226Abstract: 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: June 6, 1996Date of Patent: July 8, 1997Assignee: Hawaii Agriculture Research CenterInventors: Navzer D. Sachinala, Morton H. Litt
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Patent number: 5644041Abstract: The present invention generally relates to an alkyl glycoside of the formula (I): RCH.sub.2 O(G).sub.x H, wherein R is an alkyl group having a total of 8-12 carbon atoms and containing 2-4 groups of the formula --CH(CH.sub.3)-- in its carbon chain; G is a monosaccharide residue; and x is 1-4. The invention also relates to the use of the alkyl glycoside as a surfactant in the cleaning of hard surfaces. A composition containing an alkyl glycoside of formula (I), a complexing agent and a solubilizer is also disclosed.Type: GrantFiled: October 18, 1995Date of Patent: July 1, 1997Assignee: Akzo Nobel nvInventor: Ingegard Johansson
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Patent number: 5639733Abstract: Alkyl glycoside aqueous solutions, which satisfy the following conditions (a) and/or (b):(a) the solution is maintained at a pH value exceeding 7, and(b) the solution contains a water-soluble alcohol, are highly stable with respect to microbial activities, such as putrefaction and fungal growth, and are useful as surface active agents.Type: GrantFiled: November 14, 1994Date of Patent: June 17, 1997Assignee: Kao CorporationInventors: Toyomi Koike, Hiroshi Nagumo, Akira Yamamuro, Yukinaga Yokota
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Patent number: 5635611Abstract: A process for producing a saccharide carboxylic acid or a salt thereof characterized in that a microorganism belonging to the genus Pseudogluconobacter and capable of oxidizing a hydroxymethyl group and/or hemiacetal hydroxyl-associated carbon atom to a carboxyl group, or an artifact derived from the microorganism, is permitted to act on a hydroxymethyl and/or hemiacetal hydroxyl-containing saccharide or saccharide derivative to produce and accumulate the corresponding carboxylic acid and the carboxylic acid so accumulated is harvested and novel saccharide carboxylic acids produced by the above production method, and by the process, from a broad range of saccharides, saccharic acids having carboxyl groups derived from hydroxymethyl and/or hemiacetal OH groups can be produced with high selectivity and in good yield, the resultant saccharide acids are resistant to enzymatic degradation and have improved water solubility, among other characteristics.Type: GrantFiled: April 10, 1995Date of Patent: June 3, 1997Assignee: Takeda Chemical Industries, Ltd.Inventors: Toshihiro Ishiguro, Masahide Oka, Takamasa Yamaguchi, Ikuo Nogami
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Patent number: 5635610Abstract: A process for producing a saccharide carboxylic acid or a salt thereof characterized in that a microorganism belonging to the genus Pseudogluconobacter and capable of oxidizing a hydroxymethyl group and/or hemiacetal hydroxyl-associated carbon atom to a carboxyl group, or an artifact derived from the microorganism, is permitted to act on a hydroxymethyl and/or hemiacetal hydroxyl-containing saccharide or saccharide derivative to produce and accumulate the corresponding carboxylic acid and the carboxylic acid so accumulated is harvested and novel saccharide carboxylic acids produced by the above production method, and by the process, from a broad range of saccharides, saccharic acids having carboxyl groups derived from hydroxymethyl and/or hemiacetal OH groups can be produced with high selectivity and in good yield, the resultant saccharide acids are resistant to enzymatic degradation and have improved water solubility, among other characteristics.Type: GrantFiled: April 10, 1995Date of Patent: June 3, 1997Assignee: Takeda Chemical Industries, Ltd.Inventors: Toshihiro Ishiguro, Masahide Oka, Takamasa Yamaguchi, Ikuo Nogami
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Patent number: 5627273Abstract: The present invention is directed to methods of preparing hydrophobically-terminated polysaccharide polymers. The methods utilized to prepare the hydrophobically-terminated polysaccharide polymers utilize water as the reaction solvent and do not utilize any cosolvent. The invention is also directed to hydrophobically-terminated polysaccharide polymers which are useful as deflocculants in liquid detergent compositions and to the liquid detergent compositions which contain the hydrophobically-terminated polysaccharide polymers.Type: GrantFiled: January 31, 1995Date of Patent: May 6, 1997Assignee: National Starch and Chemical Investment Holding CorporationInventors: John S. Thomaides, James Burkert
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Patent number: 5625045Abstract: High functionality, low viscosity, light colored sucrose-based polyethers are prepared by reacting a starter mixture containing i) approximately 100 parts by weight of sucrose, ii) from about 30 to about 1000 parts by weight of a low molecular weight, relatively high valency alcohol and/or an alkoxylation product of such an alcohol and iii) an alkali metal hydroxide which has been prepared at a temperature of from about 20.degree. to about 110.degree. C. with an alkylene oxide at a temperature of from about 90.degree. to about 130.degree. C. and at a pressure of from about 0.3 to about 4 bar excess nitrogen pressure. These polyether polyols are particularly useful for the production of polyurethanes, particularly rigid polyurethane foams.Type: GrantFiled: March 18, 1994Date of Patent: April 29, 1997Assignee: Bayer AktiengesellschaftInventors: Pramod Gupta, Hans-Joachim Sandhagen, Werner Betz, Ulrich Leyrer, Martin Hoppe
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Patent number: 5621094Abstract: A method of preserving delicate biological substances or organic compounds (a) in a dry state and/or (b) at elevated temperatures and/or (c) under irradiation comprises incorporating in a system containing the said substances or compounds, a sugar or a sugar derivative selected from (i) a non-reducing glycoside of a polyhydroxy compound selected from sugar alcohols and other straight chain polyalcohols, or (ii) a non-reducing oligosaccharide selected from raffinose, stachyose and melezitose. In particular, methods for preserving dehydrated agarose gels comprising adding lactitol or glucopyranosyl-mannitol or glucopyranosyl-sorbitol to the gel during formation and prior to dehydration are disclosed.Type: GrantFiled: June 8, 1994Date of Patent: April 15, 1997Assignee: Quadrant Holdings Cambridge LimitedInventors: Bruce J. Roser, Camilo Colaco