Ethers Patents (Class 536/120)
  • Patent number: 5141929
    Abstract: Ethers and/or esters of D-desosamine having the formula ##STR1## whereinn represents 0 or 1; R and R', each independently, represent linear or branched alkyl having 1-30 carbon atoms, alkenyl having 5-21 carbon atoms, cycloalkyl having 4-10 carbon atoms, cycloalkylalkyl having 5-11 carbon atoms or phenyl or arylalkyl optionally substituted; or R can represent hydrogen when n=1 and R' can represent hydrogen when n=0, the number of carbon atoms of R, R' or R+R' being equal to 9 to 33 inclusive; or R represents the aglyconic part of erythralosamine and R' represents linear or branched alkyl having 9-30 carbon atoms or alkenyl having 11-21 carbon atoms; and the .alpha. and .beta. anomers, their mixture and their salts.These compounds are usefully employed as anti-bacteria and anti-fungus agents in pharmaceutical and cosmetic compositions.
    Type: Grant
    Filed: December 6, 1989
    Date of Patent: August 25, 1992
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Michel Phillippe, Henri Sebag
  • Patent number: 5138046
    Abstract: Surface active alkylglucosides are prepared in a 2-step process from starch or starch degradation products such as polyglucose or glucose syrup, the first step consisting of reaction with a short chained alcohol, particularly butanol, while the second step comprises transacetalization with the longer chained C.sub.8-22, more particularly C.sub.12-18, alcohol, with fatty alcohols of natural origin preferably being used.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: August 11, 1992
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Willi Wuest, Rainer Eskuchen, Josef Wollman, Karlheinz Hill, Manfred Biermann
  • Patent number: 5135650
    Abstract: Highly compressible chromatographic stationary phase particles such as agarose beads are made rigid to a degree suitable for use in HPLC, and nonporous to proteins by one of two procedures. The first involves shrinking the beads with the use of an organic solvent in which the agarose bead will neither dissolve nor swell to collapse the porosity, followed by crosslinking the bead surfaces inside the collapsed pores to fix the pores in their collapsed state. The second involves filling the pores (without shrinkage of the beads) with a polymerizable substance which grafts to the pore surface, and performing the graft polymerization. The invention also extends to rigid beads, which are rendered deformable to a limited degree by coating the surface with a polymer. Finally, porous rigid beads are rendered nonporous by polymerizing a polymerizable material inside the pores in the same manner as the porous compressible beads.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: August 4, 1992
    Assignee: Bio-Rad Laboratories, Inc.
    Inventors: Stellan Hjerten, Jia-Li Liao
  • Patent number: 5135683
    Abstract: 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: Grant
    Filed: March 28, 1991
    Date of Patent: August 4, 1992
    Assignees: Arco Chemical Technology, L.P., CPC International Inc.
    Inventor: Charles F. Cooper
  • Patent number: 5136031
    Abstract: A process for the chlorination of sucrose or a derivative thereof, comprises reaction of the sucrose or derivative thereof with thionyl chloride and a nitrogen base at a ratio of about 1 molar equivalent (ME) of thionyl chloride and about 1 ME of base for every ME of free hydroxyl, in a non-reactive moderately polar solvent. The process is particularly suitable for the preparation of sucralose.
    Type: Grant
    Filed: July 9, 1990
    Date of Patent: August 4, 1992
    Assignee: Tate & Lyle Public Limited Company
    Inventors: Riaz A. Khan, George H. Sankey, Philip J. Simpson, Nicholas M. Vernon
  • Patent number: 5134230
    Abstract: A disaccharide compound represented by formula (I): ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are as defined in the specification and a salt thereof are disclosed. The compound exhibits excellent antitumor activity and low toxicity and is useful as an antitumor agent.
    Type: Grant
    Filed: January 18, 1991
    Date of Patent: July 28, 1992
    Assignee: Daiichi Pharmaceutical Co., Ltd.
    Inventors: Tsuneo Kusama, Tsunehiko Soga, Tetsuo Shiba
  • Patent number: 5128462
    Abstract: Alkyl and hydroxyalkyl ethers of polygalactomannans are further modified with long chain haloalkanoic acids. The resulting derivatized polygalactomannans are useful as thickening agents in aqueous systems, particularly in combination with surfactants at acidic pH.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: July 7, 1992
    Assignee: Rhone-Poulenc Inc.
    Inventor: George M. Zody
  • Patent number: 5126493
    Abstract: Alkoxylates of active hydrogen compounds having a peaked molecular weight distribution are prepared by reacting the active hydrogen compound with an alkylene oxide of from 2 to 4 carbon atoms using iron oxides as alkoxylation catalysts.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: June 30, 1992
    Inventors: Wolfgang Hoelderich, Jochen Houben, Gerhard Wolf, Michael G. Kinnaird
  • Patent number: 5126438
    Abstract: 6,6'-dihalo-6,6'-dideoxy-1',2,3,3',4,4'-hexa-O-methylsucrose compounds are disclosed as useful intermediates for the synthesis of water-absorbent polyethers. These compounds may also be used as intermediates in the preparation of other difunctional monomers and metal complexing agents from sucrose.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: June 30, 1992
    Assignee: Hawaiian Sugar Planters' Association
    Inventor: Navzer D. Sachinvala
  • Patent number: 5126441
    Abstract: Bisglycosides IGly--O--CHR.sup.2 --(CH.sub.2).sub.p --(XR.sup.1).sub.n --(CH.sub.2).sub.q --(CHR.sup.3).sub.m --O--Gly IwhereX is C--R.sup.4 or N,R.sup.1 is C.sub.1 -C.sub.30 -alkyl, C.sub.2 -C.sub.30 -alkenyl, O--C.sub.1 -C.sub.30 -alkyl or O--C.sub.2 -C.sub.30 -alkenyl when X is C--R.sup.4, and is CO--C.sub.1 -C.sub.30 -alkyl or CO--C.sub.2 -C.sub.30 -alkenyl when X is N,R.sup.2 to R.sup.4 are each hydrogen, C.sub.1 -C.sub.30 -alkyl or C.sub.2 -C.sub.30 -alkenyl,n is from 1 to 3,m is 0 or 1,p and q are each from 0 to 2 andGly is a mono- or disaccharide composed of aldopentoses,aldohexoses and/or ketohexoses,are used as surfactants or emulsifiers in detergents, cleaning agents and toiletries.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: June 30, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Wolf, Richard R. Schmidt, Karin Jankowski, Andreas Terjung
  • Patent number: 5126437
    Abstract: Compounds of the formula ##STR1## in which R.sup.1 represents saturated, unsaturated or anhydro desoxypentosyl, desoxyhexosyl or didesoxyhexosyl, where the OH functions of the sugar are optionally protected, andR.sup.2 represents straight-chain or branched or heterosubstituted alkyl having up to ten carbon atoms andR.sup.3 represents straight-chain or branched or heterosubstituted alkyl having up to ten carbon atoms andX represents halogens andR.sup.4 represents straight-chain or branched or heterosubstituted alkyl having up to ten carbon atoms.Such compounds are useful as highly selective cytostatics in cancer therapy.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: June 30, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz-F. Tietze, Manfred Neumann, Roland Fischer
  • Patent number: 5124446
    Abstract: Betaine group-containing polysaccharides with recurring anhydroglucose units of the average, general formula ##STR1## are disclosed. In this formula the R.sup.1 groups are the same or different and represent methyl, (C.sub.n H.sub.2n O).sub.m R.sup.2 or ##STR2## in which n=2 or 3, m=0 to 10, p=0 to 10 and R.sup.2 is a hydrogen atom or the betaine group ##STR3## in which R.sup.3 and R.sup.4 are the same or different and represent an alkyl group with 1 to 4 carbon atoms and R.sup.5 is a divalent aliphatic hydrocarbon group with 1 to 10 carbon atoms, with the proviso that at least 0.5% of the R.sup.1 groups in the polysaccharide molecule represent the betaine group.Also disclosed is a method for the synthesis of these compounds and their use in cosmetic preparations, especially for the care of the hair. In addition, novel compounds of the general formula ##STR4## are disclosed as intermediates in which the substituents R.sup.3, R.sup.4 and R.sup.5 have the above meaning.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: June 23, 1992
    Assignee: Th. Goldschmidt AG
    Inventors: Burghard Gruning, Klaus Hoffmann, Gotz Koerner, Hans-Joachim Kollmeier
  • Patent number: 5122601
    Abstract: A process for manipulating any polyhydroxy compound bearing two or more primary and secondary hydroxyl groups to expose only the primary hydroxyl groups, while blocking all interfering secondary hydroxyl groups as their methyl or other alkyl ethers. More particularly, the present invention relates to the synthesis of 2,3,3',4,4'-penta-O-methylsucrose by using this method.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: June 16, 1992
    Assignee: Hawaiian Sugar Planters'Association
    Inventor: Navzer D. Sachinvala
  • Patent number: 5120836
    Abstract: A 6,6'-diamino-6,6'-dideoxy-1',2,3,3',4,4'-hexa-O-methylsucrose compound is disclosed which is useful as an intermediate compound to make water-absorbent polyamides, polyurethanes and polyamines.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: June 9, 1992
    Assignee: Hawaiian Sugar Planter's Association
    Inventor: Navzer D. Sachinvala
  • Patent number: 5118804
    Abstract: A process for preparing alkykl-1-thio-.alpha.,.beta.-glycosides and alkyl glycosides is described. The glycosides are prepared from a saccharide selected from monosaccharides and reducible di- and oligo-saccharides. The saccharide is reacted with either a thiol to produce an alkyl-1-thio-.alpha.,.beta.-glycoside or an alcohol to produce an alkyl glycoside in the presence of the solvent and reagent poly-(hydrogen fluoride)-pyridinium. Novel alkyl-1-thio-.alpha.,.beta.-glycosides prepared by the process of the invention are characterized in that they are in the form of a mixture of .alpha. and .beta. anomers. The alkyl-1-thio-.alpha.,.beta.-glycosides having a long alkyl chain are useful as nonionic detergents, in particular in the extraction of membrane proteins.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: June 2, 1992
    Assignee: Beghin-Say, SA
    Inventors: Jacques Defaye, Andree Gadelle, Christian Pedersen
  • Patent number: 5116961
    Abstract: A 1',6,6'-trimethylacryloyl-2,3,3',4,4'-penta-O-methylsucrose compound is disclosed. This compound is prepared by treating 2,3,3',4,4'-penta-O-methylsucrose with methacryloyl chloride in the presence of triethylamine and tetrahydrofuran. This compound is used as a crosslinking agent in the preparation of polymers.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: May 26, 1992
    Assignee: Hawaiian Sugar Planters' Association
    Inventor: Navzer Sachinvala
  • Patent number: 5114619
    Abstract: This invention is a process for the preparation of a polyol having an equivalent weight of 200 to 5000 by the reaction of a monoepoxy compound with an initiator containing an active hydrogen atom in the presence of a catalyst substance selected from the group consisting of barium, strontium and their oxides, hydroxides, hydrated hydroxides or monohydroxide salts, and mixtures thereof. The process comprises adding water during the reaction of the monoepoxy compound with the initiator. The quantity of water added is one percent or less by weight of the total weight of monoepoxy compound to be reacted with the initiator.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: May 19, 1992
    Assignee: The Dow Chemical Company
    Inventor: A. J. Heuvelsland
  • Patent number: 5106967
    Abstract: Disclosed are novel 5-C-hydroxymethylhexose compounds and their derivatives which exhibit sugar-like functionality when used in food compositions. The derivatives include stereoisomers, di-, tri-, and polysaccharides, alkyl glycosides, polyol, and alditol derivatives. Also disclosed are sugar substitute compositions and food compositions containing these compounds and their derivatives.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: April 21, 1992
    Assignee: The Procter & Gamble Company
    Inventor: Adam W. Mazur
  • Patent number: 5095104
    Abstract: A glucofuranose derivative substituted at the 3,5,6- or 3,6-positions with a radical that provides an anionic charge at physiological pH values is disclosed, as are pharmaceutical compositions, and methods of making and using the same. The compounds are useful in treating inflammation, and particularly conditions that involve neutrophil influx; they are also useful in inhibiting peptic ulcer formation.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: March 10, 1992
    Inventor: Paul Gordon
  • Patent number: 5077073
    Abstract: The present invention relates to a fat substitute comprising an ethoxyloted sugar or sugar alcohol sucrose fatty acid ester. Between 1 and about 50 alkoxyl groups are attached by ether linkages to each polyol molecule. Each ethoxylated polyol is esterified with between about 6 and about 8 fatty acid groups, the fatty acids containing between about 2 and about 24 carbon atoms. The invention also relates to a low calorie fat-containing food composition which comprises: (a) non-fat ingredients; and (b) fat ingredients, from about 10% to about 100% by weight of said fat ingredients consisting essentially of the above-described fat substitute.
    Type: Grant
    Filed: August 25, 1989
    Date of Patent: December 31, 1991
    Assignee: The Proctor & Gamble Company
    Inventors: John L. Ennis, Peter W. Kopf, John R. Powell, Stephen E. Rudolph, Martin F. van Buren
  • Patent number: 5071598
    Abstract: Compositions for cryopreservation of phosphoglyceride-containing biological and synthetic membranes are provided in which a lipophilic anchor molecule is modified by the attachment of a preferably carbohydrate moiety placed at a predetermined, variable distance from the hydrophobic portion of the molecule by means of a hydrophilic linker unit. A method for the use of the compositions is also provided.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: December 10, 1991
    Assignee: California Institute of Technology
    Inventors: John D. Baldeschwieler, Raymond P. Goodrich, Jr.
  • Patent number: 5070125
    Abstract: Polyether polyols having an equivalent weight of from about 200 to about 5000 are prepared by the process of this invention. The process uses barium- or strontium-containing alkoxylation catalysts to provide products with reduced unsaturation in comparison to similar products produced with potassium hydroxide catalysis. The use of these catalysts also increases the capping efficiency with ethylene oxide to provide products with a higher primary hyroxyl content for the same weight percentage of ethylene oxide cap.
    Type: Grant
    Filed: January 8, 1991
    Date of Patent: December 3, 1991
    Assignee: The Dow Chemical Company
    Inventor: Albert J. Heuvelsland
  • Patent number: 5057605
    Abstract: Sialocylglycerolipids represented by the following general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a group CH.sub.3 CO--; R.sup.2 represents an alkali metal, a hydrogen atom or a lower alkyl group; R.sup.3 represents a hydrogen atom or a group C.sub.n H.sub.2n+1 -- (n is an integer ranging from 1 to 30); and R.sup.4 represents a group C.sub.m H.sub.2n+1 -- (m is an integer ranging from 1 to 30) are herein disclosed. They are prepared by treating a corresponding compound in an alkaline aqueous solvent. The method makes it possible to provide these compounds in a high yield by a simple processes.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: October 15, 1991
    Assignee: Mect Corporation
    Inventors: Shoji Yoshimura, Yuzi Matsuzaki, Mamoru Sugimoto, Masayoshi Ito, Yoshiyasu Shitori, Tomoya Ogawa
  • Patent number: 5055571
    Abstract: The present invention pertains to a method of purifying crude polyol fatty acid polyesters, in particular sugar polyesters, comprising, preferably more than one, alkaline washing treatments at pH of at least 12.5, optionally in combination with water and/or acid washing treatments and further conventional refining steps. By this method better color-removal and stability against high-temperature discoloring is achieved.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: October 8, 1991
    Assignee: Van den Bergh Foods Co., Division of Conopco Inc.
    Inventor: Gerard J. Van Lookeren
  • Patent number: 5049664
    Abstract: A trehalose derivative of the formula: ##STR1## wherein one, two, three or four of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are independently selected from the group consisting of C.sub.1-40 aliphatic acyl groups and all the rest of them are hydrogen atoms,with the proviso that:a) when one of them is C.sub.1-40 aliphatic acyl group, then it is not 2-palmitoyl or 6-aliphatic acyl,b) when two of them are C.sub.1-40 aliphatic acyl groups, then they are not located at corresponding positions with each other,c) when three of them are C.sub.1-40 aliphatic acyl groups, then they are not 2,3,2'-tripalmitoyl, andd) when four of them are C.sub.1-40 aliphatic acyl groups, then they are not located at corresponding positions with each other or at 2,3,4,2'- or 2,3,6,2'-positions.The compounds of the above formula have anti-tumor activity.
    Type: Grant
    Filed: August 16, 1989
    Date of Patent: September 17, 1991
    Assignee: Sawai Pharmaceutical Co., Ltd.
    Inventors: Junji Yoshinaga, Takeshi Shogaki, Takao Kakita, Hiromi Ozeki, Yoshiko Kato
  • Patent number: 5047518
    Abstract: Herbicidal and/or plant-growth regulatory compositions comprising, together with a carrier and/or surface-active agent, an effective amount of at least one herbicidal and/or plant growth regulatory active agent selected from compounds of formula (I) ##STR1## (in which R represents an optionally substituted aralkyl group,X represents an O--, N-- or S-linked organic group, an optionally substituted hydrocarbyl group, a halogen atom, a hydroxy, amino, alkoxyamino, nitro, cyano, azido, sulpho or phospho group, or together with the group R.sup.2e, X may represents a ketonic oxygen atom --O-- or a group of formula --CH.sub.2 O--;R.sup.1e represents a hydrogen atom or an optionally substituted hydrocarbyl group, or a formyl group;R.sup.2e represents a hydrogen atom, a hydroxy group or an optionally substituted hydrocarbyl or O-linked hydrocarbyl group,or, together with the group X, R.sup.2e may represent a ketonic oxygen atom --O-- or a group of formula --CH.sub.2 O--;R.sup.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: September 10, 1991
    Assignee: Her Majesty the Queen in right of New Zealand
    Inventors: Richard H. Furneaux, Ronald F. Henzell, Peter C. Tyler
  • Patent number: 5043438
    Abstract: The present invention pertains to a process for the synthesis of polyol fatty-acid esters by reacting a polyol and a fatty-acid lower-alkyl ester under substantially solvent-free conditions in the presence of a transesterification catalyst and an emulsifier. The process comprises a continuous initial reaction stage in a first reaction zone wherein a steady-state conversion is achieved of over 1% and a further reaction stage in which the reaction mixture from said first zone is further reacted to the required polyol fatty-acid esters in one or more subsequent reaction zones.
    Type: Grant
    Filed: February 9, 1990
    Date of Patent: August 27, 1991
    Assignee: Van den Bergh Foods Co., Division of Conopco Inc.
    Inventor: Markus G. Buter
  • Patent number: 5041427
    Abstract: Compounds are disclosed which are useful in a method of treating animals to protect them from the toxic effects of Gram negative endotoxin. They include the diphosphoryl lipid A (DPLA) which can be obtained from R. sphaeroides ATCC 17023 grown at about 26.degree. C.
    Type: Grant
    Filed: January 19, 1990
    Date of Patent: August 20, 1991
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Kuni K. Takayama, Nilofer Qureshi
  • Patent number: 5037969
    Abstract: The invention provides a compound of the formula (I): R--O--CH.sub.2 CH.sub.2 O.sub.m CH.sub.2).sub.n --Z wherein R is a glycosyl group, m is an optional positive integer, n is an integer from 1 to 3 and Z is --CHO, --CH.sub.2 OH or --COOH.The compound of the formula (I'): R--O--CH.sub.2 CH.sub.2 O.sub.m CH.sub.2).sub.n --CHO wherein R, m and n are as defined above and the formula (I"'): R--OCH.sub.2 CH.sub.2 O.sub.m CH.sub.2).sub.n --COOH wherein R, m and n are as defined above is useful as a chemically modifying agent for protein.The compound of the formula (I"): R--O--CH.sub.2 CH.sub.2 O.sub.m CH.sub.2).sub.n --CH.sub.2 OH wherein R, m and n are as defined above is useful as a protein fractionating agent.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: August 6, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Isao Minami, Hayao Ueno, Masahiko Fujino
  • Patent number: 5034516
    Abstract: A compound X-Y wherein X comprises sialic acid, a sialic acid derivative or an oligosaccharide terminating in a sialic acid or sialic acid derivative if multibranched at the end of at least the largest branch, and, Y represents coupling means which allows an antibody to be raised to X when the compound is coupled to a carrier through the coupling means Y and the coupled compound used to raise said antibody. These compounds show utility in that they, and antibodies raised against these, can be used in detecting and diagnosing cancers.
    Type: Grant
    Filed: August 4, 1987
    Date of Patent: July 23, 1991
    Assignee: University of Ottawa
    Inventors: Rene Roy, Craig A. Laferriere
  • Patent number: 5034519
    Abstract: The invention relates to new oligosaccharides comprising the structure (D-ribose-D-ribitol-phosphate).sub.m, (D-ribitol-phosphate-D-ribose).sub.m or (phosphate-D-ribose-D-ribitol).sub.m, m being 2,3,4 . . . 19 or 20, to immunogens containing such oligosaccharide, to vaccines containing such immunogens and to methods for preparing such oligosaccharides, immunogens and vaccines. The vaccine is very suitable for treating infections caused by Haemophilus influenzae type b.
    Type: Grant
    Filed: December 29, 1987
    Date of Patent: July 23, 1991
    Assignee: De Staat Der Nederlanden
    Inventors: Eduard C. Beuvery, Adolf Evenberg, Jan T. Poolman, Jacobus H. van Boom, Peter Hoogerhout, Constant A. A. van Boeckel
  • Patent number: 5032682
    Abstract: Silated polysaccharides having 0.005 to 2.0 silyl molar substitution per anhydrosaccharide unit form water resistant films when cast from aqueous solution and dried in the presence of atmospheric carbon dioxide. These films are soluble in aqueous caustic. A preferred water soluble polymer is a cellulose ether with 0.005 to 1.0 silyl substitution.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: July 16, 1991
    Assignee: Aqualon Company
    Inventor: Arjun C. Sau
  • Patent number: 5023329
    Abstract: Process which comprises reacting sucrose with a di-(hydrocarbyl)tin oxide in an inert organic reaction vehicle with removal of water for a period of time and at a temperature sufficient to produce a 1,3-di-(6-O-sucrose)-1,1,3,3-tetra(hydrocarbyl)distannoxane.
    Type: Grant
    Filed: April 23, 1990
    Date of Patent: June 11, 1991
    Assignee: Noramco, Inc.
    Inventors: David S. Neiditch, Nicholas M. Vernon, Robert E. Wingard, Jr.
  • Patent number: 5017697
    Abstract: A process for recovering, in a purified form, sucrose fatty acid esters having a high HLB included in a reaction mixture formed by a reaction of sucrose and a fatty acid alkyl ester in an organic solvent as reaction medium in the presence of a catalyst, which comprises adjusting the reaction mixture from which a part of the organic solvent may be previously removed and to which water is added to form an aqueous solution, to a neutral pH region, adding a neutral salt and sucrose to the solution to precipitate the sucrose fatty acid esters, separating and washing the precipitate with an acidic water, and subjecting the washing liquid to ultrafiltration. The concentrate obtained by ultrafiltration may be spray-dried to form a dry powder of the sucrose esters having high HLB, and the liquid obtained by separating the precipitate may be contacted with a reverse osmosis membrane to recover sucrose.
    Type: Grant
    Filed: June 28, 1989
    Date of Patent: May 21, 1991
    Assignee: Dai Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 5011922
    Abstract: A process for purifying sucrose fatty acid esters included in a reaction mixture formed by a reaction of sucrose and a fatty acid alkyl ester in an organic solvent as reaction medium in the presence of a catalyst, which comprises adjusting the reaction mixture from which a part of the organic solvent as reaction medium may be previously removed and to which water is added to form an aqueous solution, to a neutral pH region, adding a neutral salt and sucrose to the solution to precipitate the sucrose fatty acid ester, filtering off the precipitate, and washing the precipitate with an acidic water. The washed precipitate in the form of slurry is spray-dried to form a dry powder, and the filtrate is contacted with a reverse osmosis membrane to recover sucrose. According to the invention, purified sucrose fatty acid esters can be obtained from the reaction mixture without using an organic solvent as purification solvent, while sucrose can be recovered in high yield.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: April 30, 1991
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 5010187
    Abstract: Polyether polyols having an equivalent weight of from about 200 to about 5000 are prepared by the process of this invention. The process uses barium- or strontium-containing alkoxylation catalysts to provide products with reduced unsaturation in comparison to similar products produced with potassium hydroxide catalysis. The use of these catalysts also increases the capping efficiency with ethylene oxide to provide products with a higher primary hydroxyl content for the same weight percentage of ethylene oxide cap.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: April 23, 1991
    Assignee: Dow Chemical Company
    Inventor: Albert J. Heuvelsland
  • Patent number: 5008253
    Abstract: Novel derivatives are disclosed as obtained from chondroitin sulfate, dermatan sulfate and hyaluronic acid, having a molar ratio between sulfate groups and carboxylic groups like that of heparin and furthermore characterized by possessing, as the heparin, the sulfoamino group at the carbon atom at the 6 position of hexosamine.The novel compounds show a very remarkable clearing activity in comparison with the starting mucopolysaccharides, this activity being similar and for some derivatives comparable with that of heparin.Moreover, differently from what normally happens upon sulfating the sulfomucopolysaccharides, the anticoagulating activity of the novel compounds is negligible or anyhow very reduced.The compounds of the present invention find use in the therapy of arteriosclerosis.
    Type: Grant
    Filed: May 2, 1989
    Date of Patent: April 16, 1991
    Assignee: Crinos Industria Farmacobiologica S.p.A.
    Inventors: Benito Casu, Giangiacomo Torri, Annamaria Naggi, Marisa Mantovani, Rodolfo Pescador, Roberto Porta, Giuseppe Prino
  • Patent number: 5008387
    Abstract: From a reaction mixture obtained by reaction of sucrose and a fatty acid alkyl ester in the presence of a catalyst, a purified sucrose fatty acid ester is prepared without using organic solvents for purification by adding water to the reaction mixture and subjecting the resulting aqueous solution to ultrafiltration, thereby removing the unreacted sucrose, the catalyst or a salt derived from the catalyst, and the volatile component used as the reaction medium together with water. A powder of the purified sucrose fatty acid ester is easily, economically and safely prepared by subjecting the aqueous solution remaining in the ultrafiltration to reverse osmosis and spray-drying the resulting concentrate.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: April 16, 1991
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 5006647
    Abstract: A disaccharide compound represented by formula (I): ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are as defined in the specification and a salt thereof are disclosed. The compound exhibits excellent antitumor activity and low toxicity and is useful as an antitumor agent.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: April 9, 1991
    Assignee: Daiichi Seiyaku Co., Ltd.
    Inventors: Tsuneo Kusama, Tsunehiko Soga, Tetsuo Shiba
  • Patent number: 5001231
    Abstract: Carboxymethylhydroxyethyl (CMHEC), starch and guar are preferred polysaccharides providing at least a 1% solution viscosity of 1000 cps at 25 C. An invert emulsion for oil drilling or paper manufacture comprises on a weight percent basis:______________________________________ Diesel, mineral or paraffin oil 40-60 Imidazole surfactant 1-4 Water 0-10 Organophilic clay 0.5-5.
    Type: Grant
    Filed: November 20, 1989
    Date of Patent: March 19, 1991
    Assignee: Aqualon Company
    Inventor: Jose Zapico
  • Patent number: 4996310
    Abstract: There is described and claimed a polyol-polyether having a high content of ethylene oxide and low viscosity, greatly suitable for use in the preparation of rigid polyurethane foam.The polyol-polyether of this invention is of high quality and low cost, as well as having low viscosity, thus expediting handling in foaming machines.
    Type: Grant
    Filed: March 10, 1989
    Date of Patent: February 26, 1991
    Assignee: Polioles, S. A. de C.U.
    Inventor: Roberto M. Acosta
  • Patent number: 4996309
    Abstract: A process for preparing sucrose fatty acid esters by reacting sucrose and a fatty acid alkyl ester in an aqueous reaction system in the presence of a catalyst, adding water to the reaction mixture to dissolve it, adjusting the reaction mixture to a neutral ph region, adding a neutral salt to the solution to precipitate the sucrose fatty acid esters, separating and washing the precipitate with an acidic water, and subjecting the washing liquid to ultrafiltration. The precipitate washed with the acidic water is spray-dried in the form of an aqueous slurry to give a dry powder of the sucrose esters having low HLB, and the concentrate obtained by ultrafiltration is spray-dried to form a dry powder of the sucrose esters having high HLB, and the liquid obtained by separating the precipitate is contacted with a reverse osmosis membrane to recover sucrose. According to the invention, purifed sucrose fatty acid esters can be obtained without using an organic solvent, while sucrose can be recovered in high yield.
    Type: Grant
    Filed: October 3, 1989
    Date of Patent: February 26, 1991
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 4996306
    Abstract: Glycoside products are successfully prepared directly from aqueous saccharide solutions or syrups, and with acceptably low levels of undesired homopolymerized saccharide by-products, by dissolving same in the desired alcohol reactant or in an alcohol reactant plus glycoside product mixture and contacting the resulting homogeneous aqueous saccharide solution and alcohol-containing reaction medium with an acid catalyst in a fashion such that no separate or distinct, substantially alcohol reactant-free aqueous saccharide solution-containing phase is permitted to come into contact with said acid catalyst material under conditions conductive to homopolymerization of said saccharide reactant.
    Type: Grant
    Filed: April 5, 1988
    Date of Patent: February 26, 1991
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Robert S. McDaniel, Jr., Donald L. Johnson
  • Patent number: 4992539
    Abstract: A cold-water-swellable granular starch which affords aqueous solutions or dispersions having high-viscosity and/or excellent clarity is provided. In one embodiment, the granular starch is made cold-water swellable by contact with aqueous alcohol, then derivatized with an .alpha.-halocarboxylic acid, and then isolated under condition which inhibit esterification of the granular starch, e.g. high pH, to afford a starch that has excellent paste clarity. In other embodiments, the cold-water-swellable granular starch is crosslinked to afford a starch that has very high paste viscosity.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: February 12, 1991
    Assignee: A. E. Staley Manufacturing Company
    Inventors: Norman A. Portnoy, James E. Eastman
  • Patent number: 4992536
    Abstract: Polycationic polysaccharide derivatives containing more than one cationic substituent per substituted hydroxyl group are prepared by a site selective reaction of a cationic polysaccharide derivative with a suitable cationic reagent at a pH from 7.0 to 9.0. Suitable reagents include cationic alkyl, aryl, alkaryl, cycloaliphatic, or heterocyclic amines, and polymer thereof, which selectively react with a cationic substituent rather than a hydroxyl group of the cationic polysaccharide derivative. The polycationic polysaccharide derivatives prepared from these reagents are useful in the manufacture of paper.
    Type: Grant
    Filed: October 31, 1989
    Date of Patent: February 12, 1991
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Robert L. Billmers, Daniel B. Solarek, Ralph M. Trksak
  • Patent number: 4990603
    Abstract: The present invention relates to sialic acid derivatives. According to the present invention, there is provided sialic acid derivatives having the general formula (I): ##STR1## wherein, R.sup.1 represents hydrogen, an acetyl group, a trityl group, ##STR2## (R.sup.5 represents hydrogen or an acetyl group and R.sup.6 represents hydrogen, sodium or a methyl group).R.sup.2 represents hydrogen or an acetyl group,one of R.sup.3 and R.sup.4 represents ##STR3## (R.sup.7 represents a hydrogen atom or an acetyl group, R.sup.8 represents a hydrogen atom, an acetyl group or a benzyl group, R.sup.9 represents a hydrogen atom, an acetyl group, a benzyl group or ##STR4## wherein R.sup.10 represents a hydrogen atom or a benzoyl group), while the other represents --COOR.sup.11 wherein R.sup.11 represents hydrogen, sodium, or a methyl group.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: February 5, 1991
    Assignee: Mect Corporation
    Inventors: Tomoya Ogawa, Mamoru Sugimoto, Masaaki Numata, Shoji Yoshimura, Masayoshi Ito, Yoshiyasu Shitori
  • Patent number: 4990605
    Abstract: A method of manufacturing alkyloligoglycosides. Alkyloligoglycosides and alkylglycosides having alkyl groups with 8 to 24 carbon atoms, which products are of interest as surface active agents in home economics, and in the cosmetics industry, can be manufactured by glycosidation and transglycosidation. Light-colored alkyloligoglycosides and alkylglycosides can be manufactured by treating their solution in alcohols with activated carbon, distilling off the solvent, and bleaching the distillation residue or an aqueous solution of the residue with a peroxide compound.
    Type: Grant
    Filed: May 11, 1988
    Date of Patent: February 5, 1991
    Assignee: Huels Aktiengesellschaft
    Inventor: Harald Lueders
  • Patent number: 4990609
    Abstract: Sulfoethyl cellulose prepared by addition of an alkylating agent and subsequent addition of alkali shows particularly valuable properties.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: February 5, 1991
    Assignee: Wolff Walsrode AG
    Inventors: Dieter Herzog, Klaus Balser, Klaus Szablikowski
  • Patent number: 4987271
    Abstract: A method for purifying a polyoxyalkylene alcohol, which comprises treating with a treating agent consisting essentially of a pH buffer, a polyoxyalkylene alcohol containing a double metal cyanide complex catalyst, synthesized by ring-opening polymerization of an alkylene oxide in the presence of said catalyst, and then removing the catalyst and the treating agent from the polyoxyalkylene alcohol.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: January 22, 1991
    Assignee: Asahi Glass Company, Ltd.
    Inventors: Takashi Watabe, Hiromitsu Takeyasu, Takao Doi, Nobuaki Kunii
  • Patent number: 4985551
    Abstract: A process for the ion exchange of polyols for catalyst removal wherein said catalyst is an alkali hydroxide or alkoxide comprising the sequential steps of:(a) mixing the polyether molecule having a molecular weight of 500-10,000 with water,(b) blending into the product of (a) a sufficient amount of a lower aliphatic alcohol to break the emulsion formed in step (a),(c) passing the product of step (b) through a macroporous cation exchange resin to obtain a purified polyether molecule, methanol, and water.The product of (c) may be further subjected to stripping to produce the purified polyether polyols.
    Type: Grant
    Filed: December 29, 1988
    Date of Patent: January 15, 1991
    Assignee: BASF Corporation
    Inventors: John G. Perry, Walter A. Spelyng