Carboxylic Patents (Class 536/119)
-
Patent number: 5061792Abstract: Chitosan is converted to dry, free-flowing, water-soluble chitosan salts by heterogeneous reaction between particulate chitosan suspended in about 5 to about 50 parts by weight of a C.sub.1 to C.sub.3 monohydric alcohol containing an amount of water sufficient to raise the dielectric constant of the alcohol to at least about 30 and not more than about 40. Operable acids are slected from defined aliphatic and aromatic carboxylic, aromatic sulphonic, and inorganic acids having a first hydrogen pKa in water at room temperature of less than about 5.Type: GrantFiled: December 18, 1989Date of Patent: October 29, 1991Assignee: University of DelawareInventors: Charles J. Albisetti, John E. Castle
-
Patent number: 5055571Abstract: 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: GrantFiled: December 5, 1988Date of Patent: October 8, 1991Assignee: Van den Bergh Foods Co., Division of Conopco Inc.Inventor: Gerard J. Van Lookeren
-
Patent number: 5049664Abstract: 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: GrantFiled: August 16, 1989Date of Patent: September 17, 1991Assignee: Sawai Pharmaceutical Co., Ltd.Inventors: Junji Yoshinaga, Takeshi Shogaki, Takao Kakita, Hiromi Ozeki, Yoshiko Kato
-
Patent number: 5047518Abstract: 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: GrantFiled: April 10, 1990Date of Patent: September 10, 1991Assignee: Her Majesty the Queen in right of New ZealandInventors: Richard H. Furneaux, Ronald F. Henzell, Peter C. Tyler
-
Patent number: 5043438Abstract: 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: GrantFiled: February 9, 1990Date of Patent: August 27, 1991Assignee: Van den Bergh Foods Co., Division of Conopco Inc.Inventor: Markus G. Buter
-
Patent number: 5041427Abstract: 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: GrantFiled: January 19, 1990Date of Patent: August 20, 1991Assignee: Wisconsin Alumni Research FoundationInventors: Kuni K. Takayama, Nilofer Qureshi
-
Patent number: 5041226Abstract: A separation agent essentially comprises an aliphatic or aromatic ester of a polysaccharide, except for cellulose acetate and an aromatic ester of cellulose. It is useful for separation of various chemical substances, especially optical resolution of optical isomers.Type: GrantFiled: November 2, 1989Date of Patent: August 20, 1991Assignee: Daicel Chemical Industries, Ltd.Inventors: Tohru Shibata, Hajime Namikoshi, Ichiro Okamoto
-
Patent number: 5034551Abstract: A process which comprises extracting 1,3-diacyloxy-1,1,3,3-tetra(hydrocarbyl) distannoxane from a mixture containing 1,3-diacyloxy-1,1,3,3-tetra(hydrocarbyl)distannoxane, a sucrose-6-ester, and polar aprotic solvent, which process comprises the steps of:(a) contacting said mixture, in the presence of a small amount of water, with an organic solvent that is substantially immiscible with water to form thereby an extraction mixture, wherein the amount of water employed is sufficient to cause efficient partitioning of said 1,3-diacyloxy-1,1,3,3-tetra(hydrocarbyl)distannoxane from a first phase comprising said polar aprotic solvent into second phase comprising said organic solvent;(b) agitating the extraction mixture for a period of time and at a temperature sufficient to form thereby a two-phase mixture wherein the preponderance of the 1,3-diacyloxy-1,1,3,3-tetra(hydrocabyl)distannoxane in the extraction mixture is contained in said second phase and essentially all of the sucrose-6-ester in the extraction mixtureType: GrantFiled: April 23, 1990Date of Patent: July 23, 1991Assignee: Noramco, Inc.Inventors: Nicholas M. Vernon, Robert E. Walkup
-
Patent number: 5030723Abstract: A substantially pure unbranched ceramide polysaccharide type 2 chain compound having the following structure: ##STR1## wherein Gal represents galactose, GlcNAc represents N-acetylglucosamine, Fuc represents fucose Glc represents glucose and Cer represents ceramide. A substantially pure unbranched ceramide polysaccharide type 2 chain compound having the following structure: ##STR2## wherein Gal represents galatose, GlcNAc represents N-acetylglucosamine. Fuc represents fucose, Glc represents glucose, Cer represents ceramide and NeuAc represents sialic acid. Antibodies that are specific to portions of the above-described compounds, wherein the portions comprise the internal .alpha.1-.fwdarw.3 fucosyl residue and/or the terminal sialic acid residue. Immuogens for producing antibodies to the above-described compounds or portions thereof. A method of actively immunizing against tumors that express the above-described compounds.Type: GrantFiled: May 31, 1988Date of Patent: July 9, 1991Assignee: The Biomembrane InstituteInventors: Edward D. Nudelman, Steven B. Levery, Mark R. Stroud, Mary Ellen K. Salvan, Sen-itiroh Hakomori
-
Patent number: 5028734Abstract: A process for the selective carbonylation of a conjugated diene by contacting with carbon monoxide in the presence of a hydroxyl-group-containing compound such as water, alcohol, phenol or carboxylic acid in liquid phase using a catalyst system formed by the combination of:(a) a palladium compound and(b) at least one organic bidentate phosphine.Type: GrantFiled: January 27, 1989Date of Patent: July 2, 1991Assignee: Shell Oil CompanyInventor: Eit Drent
-
Patent number: 5023329Abstract: 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: GrantFiled: April 23, 1990Date of Patent: June 11, 1991Assignee: Noramco, Inc.Inventors: David S. Neiditch, Nicholas M. Vernon, Robert E. Wingard, Jr.
-
Patent number: 5021562Abstract: Reactions of azide ion with 2-O-trifluoromethanesulphonates of both 3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heltono-1,5-lactone and of 3,4:6,7-di-O-isopropylidene-D-glycero-D-galactoheptono-1,5-lactone are disclosed to give predominantly 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1, 5-lactone initially which then isomerizes under moderate reaction conditions to 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1, 5-lactone.Type: GrantFiled: May 17, 1990Date of Patent: June 4, 1991Assignee: Monsanto CompanyInventors: George W. J. Fleet, Ian Bruce
-
Patent number: 5021256Abstract: Disclosed are preferred shortenings made with polyol polyesters. The Solid Fat Content curve and penetration of the shortenings is adjusted to increase smoothness and decrease graininess. Also described are food compositions that have enhanced flavors from the addition of particular sucrose polyesters.Type: GrantFiled: November 6, 1989Date of Patent: June 4, 1991Assignee: The Procter & Gamble CompanyInventors: Timothy B. Guffey, Donn N. Boatman, Susan S. Abe, Sherry R. Talkington, Marko D. Mijac
-
Patent number: 5017398Abstract: Bread spread compositions (e.g., margarine) wherein the fat portion of the composition comprises a triglyceride oil or a non-digestible oil and a solid non-digestible sucrose polyester of a mixture of short chain and long chain saturated carboxylic acids, the molar ratio of short chain:long chain radicals being from about 4:4 to about 3:5 and the degree of esterification being from about 7 to about 8.Type: GrantFiled: October 7, 1988Date of Patent: May 21, 1991Assignee: The Procter & Gamble CompanyInventors: Ronald J. Jandacek, James C. Letton
-
Patent number: 5017697Abstract: 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: GrantFiled: June 28, 1989Date of Patent: May 21, 1991Assignee: Dai Ichi Kogyo Seiyaku Co., Ltd.Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
-
Patent number: 5011922Abstract: 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: GrantFiled: June 23, 1989Date of Patent: April 30, 1991Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
-
Patent number: 5008387Abstract: 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: GrantFiled: April 14, 1989Date of Patent: April 16, 1991Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
-
Patent number: 5006514Abstract: An .alpha.,.alpha.-trehalose trimycolate represented by formula: ##STR1## (wherein R.sup.1 through R.sup.8 each represents a hydrogen atom or mycolic acid residue, and three of R.sup.1 through R.sup.8 are mycolic acid residues; these mycolic acid residues may, or may not be identical with each other).Since the said .alpha.,.alpha.-trehalose trimycolate possesses both immunopotentiating activity and antitumor activity on animals and is low in toxicity, it is expected to be applied to a protective drug against infection of various microbes, an antitumor agent and immunopotentiation at the time of decline in physical strength.Type: GrantFiled: October 2, 1987Date of Patent: April 9, 1991Assignee: Sawai Pharmaceutical Co., Ltd.Inventors: Yoshiko Kato, Junji Yoshinaga, Takeshi Shogaki, Satoko Kurano, Ikuya Yano
-
Patent number: 5006648Abstract: A process for preparing partial polyol fatty acid esters, e.g. sucrose or sorbitol esters, is improved by(1) mixing the polyol with an alkaline catalyst such as KOH, NaOH or their carbonates, preferably in aqueous solution or dissolved in C.sub.1-5 alcohols or ketones at atmospheric pressure and 10.degree.-80.degree. C.,(2) preparing a mixture of fatty acid lower alkyl esters with an emulsifier, preferably a fatty acid soap, and(3) adding the alkaline polyol solution to the mixture of (2), whereby preferably the solvent is removed during the addition of (1) to (2), e.g. at 60.degree. C. and 5 mbar.The reaction is improved so that partial polyol fatty acid esters with at most half of the polyol hydroxy groups being esterified are formed at 110.degree.-145.degree. C. within 1-4 hours.Type: GrantFiled: July 22, 1987Date of Patent: April 9, 1991Assignee: Van den Bergh Foods Co., Division of Conopco Inc.Inventors: Pleun Van der Plank, Adrianus Rozendaal
-
Patent number: 5006647Abstract: 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: GrantFiled: March 2, 1988Date of Patent: April 9, 1991Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Tsuneo Kusama, Tsunehiko Soga, Tetsuo Shiba
-
Patent number: 4996309Abstract: 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: GrantFiled: October 3, 1989Date of Patent: February 26, 1991Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
-
Patent number: 4995911Abstract: A process for recovering unreacted sucrose from a reaction mixture of sucrose and a fatty acid alkyl ester in an organic solvent as reaction medium in the presence of a catalyst in the production of a sucrose fatty acid ester 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 a neutral pH region, adding a neutral salt and sucrose to the reaction mixture to precipitate the sucrose fatty acid ester, filtering off the precipitate, and bringing the filtrate into contact with a reverse osmosis membrane to recover the unreacted sucrose. According to the invention, unreacted sucrose can be easily recovered, while the sucrose fatty acid ester not contaminated with the organic solvent as reaction medium can be obtained from the reaction mixture without using an organic solvent for purification.Type: GrantFiled: June 13, 1989Date of Patent: February 26, 1991Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
-
Patent number: 4990603Abstract: 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: GrantFiled: June 30, 1987Date of Patent: February 5, 1991Assignee: Mect CorporationInventors: Tomoya Ogawa, Mamoru Sugimoto, Masaaki Numata, Shoji Yoshimura, Masayoshi Ito, Yoshiyasu Shitori
-
Patent number: 4987223Abstract: The invention relates to derivatives with a uronic acid structure having substituents selected among a reactive group, a functionalisable group and --OH functions blocked by protective groups. These derivatives are useful for preparing glycosides, particularly enzyme substrates.Type: GrantFiled: October 27, 1982Date of Patent: January 22, 1991Assignee: Choay S.A.Inventors: Jean Choay, Jean-Claude Jacquinet, Maurice Petitou, Pierre Sinay
-
Patent number: 4985358Abstract: A method for processing glyceride fats and oils which comprises the steps of subjecting a mixture of a glyceride fat or oil and a monohydric alcohol fatty acid ester to an enzymatic ester interchange reaction; distilling the reaction mixture of the ester interchange reaction to separate a distillate from a processed glyceride fat or oil to recover the latter; subjecting the distillate to an esterification reaction to lower its acid value; and recycling the distillate for use as a starting material for the ester interchange reaction.Type: GrantFiled: March 11, 1988Date of Patent: January 15, 1991Assignee: Fuji Oil Company, Ltd.Inventors: Norio Sawamura, Takaharu Matsuo, Yukio Hashimoto
-
Patent number: 4985553Abstract: Process for the selective oxidation of di-, tri-, oligo- and polysaccharides comprising a reducing terminal function of the aldose type into polyhydroxycarboxylic acids, wherein the oxidation is carried out in an alkaline medium by means of an oxygen-containing gas, in the presence of a noble metal based catalyst selected from the group constituted by palladium, platinum, rhodium and osmium and fixed on an inert support, said catalyst being "doped" with one or several metals, or promoters, of Groups IV, V or VI of the Periodic Table.Type: GrantFiled: January 28, 1987Date of Patent: January 15, 1991Assignee: Roquette FreresInventors: Patrick M. Fuertes, Guy M. Fleche
-
Patent number: 4983731Abstract: The process uses two steps to separate the sugar ester from the crude sugar ester reaction product. The first step entails forming a precipitate of sugar ester from a mixture of alcohol, water and crude sugar ester reaction product. In a second subsequent step, the recovered sugar ester precipitate is washed with an organic solvent.Type: GrantFiled: March 17, 1989Date of Patent: January 8, 1991Assignee: Nebraska Department of Economic DevelopmentInventors: Frederick W. Wagner, Maria A. Dean, Rebecca S. de la Motte, Virginia H. Stryker
-
Patent number: 4980463Abstract: A process for the chlorination of sucrose-6-esters to produce 6',4,1'-trichlorosucrose-6-esters which comprises the steps of:(a) adding at least seven molar equivalents of an acid chloride to a reaction mixture containing a sucrose-6-ester and a tertiary amide to form initially a chloroformiminium chloride salt which subsequently forms a complex with the hydroxyl groups of the sucrose-6-ester;(b) subjecting the reaction mixture product of step (a) to an elevated temperature not higher than about 85.degree. C. for a period of time sufficient to produce a mixture of chlorinated sucrose-6-ester products consisting essentially of 6'-chlorosucrose-6-ester, 4,6'-dichlorosucrose-6-ester, and 1',6'-dichlorosucrose-6-ester; and(c) subjecting the reaction mixture product of step (b) to an elevated temperature not higher than about 125.degree. C. for a period of time sufficient to produce a chlorinated product consisting essentially of 1',4,6'-trichlorosucrose-6-ester.Type: GrantFiled: July 18, 1989Date of Patent: December 25, 1990Assignee: Noramco, Inc.Inventors: Robert E. Walkup, Juan L. Navia, Nicholas M. Vernon
-
Patent number: 4977254Abstract: Sugars and partly protected sugar derivatives are chlorinated by reaction of unprotected hydroxyl groups with thionyl chloride to form a persulphite followed by decomposition of the sulphite groups to form chlorosulphites, displacement of the chlorosulphite groups and insertion of chlorine atoms at one or more positions, characterised in that formation and displacement of the chlorosulphite groups and insertion of chlorine atoms is effected by reaction with thionyl chloride in an inert solvent in the presence of a quaternary salt of the general formula:N.sup.+ R.sup.1 R.sup.2 R.sup.3 R.sup.4 Cl.sup.- (I)wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent a lower alkyl group, and R.sup.Type: GrantFiled: August 2, 1989Date of Patent: December 11, 1990Assignee: Tate & Lyle PLCInventors: Nigel J. Homer, Graham Jackson, George H. Sankey, Philip J. Simpson
-
Patent number: 4973681Abstract: A polyol fatty acid polyester is stabilized by a polybasic oxy acid for using the polyester in safety, in a field of foods.Type: GrantFiled: October 2, 1989Date of Patent: November 27, 1990Assignees: Showa Sangyo Co., Ltd., Mitsubishi Chemical Industries Ltd.Inventor: Mutsuhito Watanabe
-
Patent number: 4973686Abstract: The invention relates to the use of selected carboxylic acid esters which are liquid under reaction conditions and correspond to general formula (I)X--COOR.sup.1 (I)in which R.sup.1 is an alkyl radical unbranched in the .alpha.-position and X is hydrogen or a group corresponding to general formula (II) ##STR1## in which R.sup.2, R.sup.3 and R.sup.4 represent fluorine and/or chlorine and one of these substituents may also be hydrogen or one or two of these substituents may also be lower alkyl, as reaction medium for the sulfonation and/or sulfatization or organic components with SO.sub.3 to light-colored reaction products.Type: GrantFiled: September 2, 1988Date of Patent: November 27, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Josef Kretschmann, Franz-Josef Carduck, Willi Wuest, Hubert Harth, Dirk Springer
-
Patent number: 4973682Abstract: The invention pertains to a process for the synthesis of polyol fatty acid polyesters comprising a two-stage transesterification of polyol to polyester, involving a pressure control such that in the first stage the esterification is not allowed to proceed beyond the mono- and/or oligoester, and in the second stage the esterification is continued to the polyester product.Type: GrantFiled: December 28, 1988Date of Patent: November 27, 1990Assignee: Lever Brothers CompanyInventor: Gerardus W. M. Willemse
-
Patent number: 4968790Abstract: Phosphates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These phosphates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphates are also disclosed.Type: GrantFiled: October 28, 1988Date of Patent: November 6, 1990Assignee: American Cyanamid CompanyInventors: Vern G. DeVries, Thomas H. Claus, Middleton B. Floyd, Jr., Semiramis Ayral-Kaloustian
-
Patent number: 4968791Abstract: The present invention relates to a process for the preparation of polyol fatty acid esters, in which fatty acid esters are reacted with a polyol having at least 4 hydroxyl groups, or an ester thereof, wherein the fatty acid soap comprises at least 75% of a short-chain fatty acid soap, having a fatty acid chain length of less than 15 carbon atoms. Further the invention relates to the use of the polyol fatty acid esters thus prepared in foodstuffs, pharmaceutical compositions, detergents and coating compositions.Type: GrantFiled: July 12, 1988Date of Patent: November 6, 1990Assignee: Lever Brothers CompanyInventor: Pleun Van Der Plank
-
Patent number: 4966966Abstract: A process for preparing a sucrose fatty acid ester by interesterification between sucrose and a lower alkanol ester or glyceride of a fatty acid in the presence of an ion exchange resin is disclosed, wherein said ion exchange resin is a cation exchange resin having a carboxyl group having been ion-exchanged with an alkali metal and/or an alkaline earth metal. A sucrose fatty acid can be prepared in a high yield through a simplified recovery and purification step.Type: GrantFiled: January 14, 1988Date of Patent: October 30, 1990Assignee: Mitsubishi Chemical Industries LimitedInventors: Keisuke Wada, Kazuhiko Onuma, Takashi Ushikubo, Tsuyoshi Ito
-
Patent number: 4963664Abstract: New amines and amides of carboxylated polysaccharides having the nitrogen of the amido and amino groups directly attached to the polysaccharides and method of making same, based on reacting in solution a material having carboxyl-containing polysaccharides, such as carboxymethyl cellulose, with ammonium donors having the general formula >NH such as primary and secondary amine reagents and with or without a reducing agent to obtain amides or amines. These products may be used for instance in biological separations, for the immobilization of proteins, for the removal of metal ions, as thickeners, and as suspension agents.Type: GrantFiled: October 26, 1989Date of Patent: October 16, 1990Assignee: Domtar Inc.Inventors: Manssur Yalpani, Magdy M. Abdel-Malik
-
Patent number: 4959466Abstract: Partially esterified oligosaccharides and polysaccharides (PEPs) of the formula [P--O--R).sub.x ].sub.n, where P is a polysaccharide having n=3-50 (preferably 3-10) C.sub.4 -C.sub.8 saccharide units, y is 0-4 (preferably 1 or 2), R is H or a C.sub.3 -C.sub.28 acyl group, and x is the degree of esterification ranging from 1-80 percent. The PEPs are used as indigestible fat substitutes (fat mimetics). They have non-caloric food values, with good organoleptic characteristics, are substantially resistant to intestinal absorption and do not appreciably hydrolyze in the digestive tract. Suitable polysaccharides are preferably selected from xanthan gum, guar gum, gum arabic, aliginates, cellulose hydrolysis products, hydroxypropyl cellulose, starch hydrolysis products, casein, Karaya gum and pectin. C.sub.5 and C.sub.6 oligosaccharides of n=3-10 units are preferred. The polysaccharides are transesterified with fatty acid methyl esters to create PEPs of a degree of esterification determined for each polysaccharide.Type: GrantFiled: January 25, 1988Date of Patent: September 25, 1990Assignee: Arco Chemical Technology, Inc.Inventor: John F. White
-
Patent number: 4956287Abstract: The process for producing an oleaginous composition of the present invention comprises transesterifying a fat containing a large amount of polybasic unsaturated fatty acid(s) as constituting fatty acid(s) with saturated fatty acid(s) and/or saturated fatty acid alcohol ester(s) with the use of a lipase having an site-specificity to thereby give symmetric triglyceride(s) wherein the fatty acid groups at the 1- and 3-positions are selectively transesterified and a polybasic unsaturated fatty acid group is present at the 2-position. The above transesterification should be carried out under such conditions as to give an oleaginous composition which comprises 40% or more of symmetric triglyceride(s) each having a polybasic unsaturated fatty acid group at the 2-position and 50% or more of completely saturated fatty acid(s) each having 16 or more carbon atoms.Type: GrantFiled: December 14, 1987Date of Patent: September 11, 1990Assignee: Asahi Denka Kogyo Kabushiki KaishaInventors: Kazuaki Suzuki, Shoji Maruzeni, Eiji Nakai, Toru Nezu
-
Patent number: 4954621Abstract: A process for producing a sucrose fatty acid polyester comprises reacting sucrose with fatty acid lower alcohol ester(s) in a solvent in the presence of an alkaline catalyst, wherein said fatty acid lower alcohol ester(s) are employed in an amount at least 5 times by mol as much as said sucrose. The alkaline catalyst component is removed from the reaction product thus obtained and the obtained sucrose fatty acid polyester-containing solution is catalytically treated with activated clay. This process enables the production of a sucrose fatty acid polyester containing an extremely small amount of ash components and having an extremely low color value. The alkaline catalyst used in this process may be recovered and reused, which further makes the process of the present invention advantageous.Type: GrantFiled: June 6, 1989Date of Patent: September 4, 1990Assignee: Mitsubushi Kasei CorporationInventors: Kazuhiko Masaoka, Yukio Kasori
-
Patent number: 4952687Abstract: The oxidative stability of esters of unsaturated fatty acids and polyols having from 4-8 hydroxyl groups, preferably of sugars or sugar alcohols, more preferably of sucrose, is improved if the esters contain an effective amount of the trans-unsaturated fatty acid chains.If more than 50% of the hydroxyl groups of the polyols are esterified, the esters can be used as low-calorie fat replacers, which in the case of sucrose with at least 4 hydroxyl groups esterified are called SPE (sucrose polyesters). If only 1-3 hydroxyl groups are esterified, the esters can act as emulsifiers.The ratio of cis:trans double bonds preferably ranges from (20:80) to (40:60), more preferably from (30:70) to (35:65). The trans-unsaturated fatty acid esters of polyols can be used in an amount of 0.5-99% of an edible composition, either as an emulsifier or as a fat replacer.Type: GrantFiled: August 18, 1987Date of Patent: August 28, 1990Assignee: Lever Brothers CompanyInventors: Janos Bodor, Geoffrey Page
-
Patent number: 4950746Abstract: Sucrose is reacted with a 1,3-di(hydrocarbyloxy)-1,1,3,3-tetra(hydrocarbyl)distannoxane to produce a 1,3-di-(6-O-sucrose)-1,1,3,3-tetra(hydrocarbyl)distannoxane, which can be acylated to produce a sucross-6-ester.Type: GrantFiled: July 18, 1988Date of Patent: August 21, 1990Assignee: Noramco, Inc.Inventor: Juan L. Navia
-
Patent number: 4946832Abstract: Cosmetic Base composition exhibiting therapeutic properties comprising an acyl fatty acid alpha-hydroxy carboxylic acid ester or alkali metal salt thereof, a sucrose fatty acid ester, and a solvent.Type: GrantFiled: July 21, 1988Date of Patent: August 7, 1990Assignee: R.I.T.A. CorporationInventors: Stephen T. Goode, Robert R. Linton, Fred Baiocchi
-
Patent number: 4942228Abstract: Polyol polyesters having reduced color content are prepared by base-catalyzed transesterification of pretreated lower (i.e., C.sub.1 -C.sub.3) alkyl fatty esters with polyols. The pretreatment comprises the steps of contacting the alkyl fatty esters (in a liquid state) with an alkoxide base, separating undissolved solids from the esters, and then distilling the esters.Type: GrantFiled: May 6, 1986Date of Patent: July 17, 1990Assignee: The Procter & Gamble CompanyInventor: Michael S. Gibson
-
Patent number: 4940787Abstract: A method for the preparation of alpha,beta-olefinic unsaturated compounds by means of carbonylation of acetylenic unsaturated compounds with carbon monoxide in the presence of a hydroxy-containing compound in liquid phase, accomplished in the presence of a catalytic system that can be formed from:(a) a palladium compound,(b) a protonic acid, and(c) an organic phosphine according to the formula: ##STR1## wherein R.sub.1 represents a heterocyclic five- or six-atom ring, comprising, at least as hetero atom, nitrogen, which may be optionally substituted and/or may form part of a larger condensed ring structure that may be optionally substituted, and wherein R.sub.2 and R.sub.3 each have the aforesaid meaning of R.sub.1 or may represent an optionally substituted aryl group.The invention further comprises novel organic phosphines and compositions containing said phosphines as wel as the catalytic systems containing said phosphines.Type: GrantFiled: November 25, 1987Date of Patent: July 10, 1990Assignee: Shell Oil CompanyInventor: Eit Drent
-
Patent number: 4931552Abstract: Polyol polyesters having reduced color content are prepared by base-catalyzed transesterification of lower (i.e., C.sub.1 -C.sub.3) alkyl fatty esters having a carbonyl content of less than about 200 ppm with polyols. The esters can be prepared by a pretreatment comprising distilling the said alkyl fatty esters (in a liquid state), preferably with a base, and discarding both the top cut in an amount that is about 5% or less and at least about 2% of the still bottoms.Type: GrantFiled: June 14, 1989Date of Patent: June 5, 1990Assignee: The Procter & Gamble CompanyInventors: Michael S. Gibson, Larry N. Hawkins, Marjorie M. Peffly, Corey J. Kenneally, Patrick J. Corrigan
-
Patent number: 4927920Abstract: This method for making sugar esters entails first reacting a sugar and an ter of that sugar having a degree of substitution greater than 2 with a Lewis acid or Lewis base catalyst in an organic solvent to form a sugar ester having a degree of substitution up to 2 and recovering the sugar ester having a degree of substitution up to 2 at ambient temperature. The recovery step must be conducted at a temperature below the distillation or boiling temperature of the organic solvent or else the DS of the resulting sugar ester will be greater than 2. This process is especially suited for sucrose esters. The reaction between the sugar and the sugar ester is conducted in the absence of a methyl ester of a fatty acid.Type: GrantFiled: November 15, 1988Date of Patent: May 22, 1990Assignee: Nebraska Department of Economic Development, State of Nebraska, U.S.A.Inventors: Frederick W. Wagner, Rebecca S. de la Motte, Maria A. Dean
-
Patent number: 4912094Abstract: Modified lipopolysaccharides, particularly de-3-0-acylated monophosphoryl lipid A and de-3-0-acylated diphosphoryl lipid A, are provided by an alkaline hydrolysis under controlled conditions which removes only the .beta.-hydroxymyristic acyl residue that is ester-linked to the reducing-end glucosamine at position 3. The modified products are less endotoxic and maintain their antigenic and immuno-stimulating properties.Type: GrantFiled: June 29, 1988Date of Patent: March 27, 1990Assignee: Ribi ImmunoChem Research, Inc.Inventors: Kent R. Myers, Alex T. Truchot
-
Patent number: 4898935Abstract: This invention relates to a method of producing sucrose fatty acid ester granules by the fluidized bed granulation and drying technique and consists in forming a fluidized bed comprising a sucrose fatty acid ester powder at a temperature not exceeding 60.degree. C., spraying the fluidized bed with an aqueous sucrose fatty acid ester solution having a concentration of 3-20% by weight, as a binder, and then drying the sprayed fluidized bed, to thereby cause granulation. In accordance with the invention, the disintegration of sucrose fatty acid ester granules during granulation and drying can be prevented and highly pure sucrose fatty acid ester granules can be obtained. The sucrose fatty acid ester granules produced by the method of the invention are incapable of forming a cloud of fine powder, and have very good dispersibility and solubility.Type: GrantFiled: January 17, 1989Date of Patent: February 6, 1990Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Shingo Nakamura, Hiroshi Nagahara
-
Patent number: 4897474Abstract: The invention concerns carbohydrate fatty acid esters with improved color and free-flow properties and a one-step process for preparing them. To prepare the products, carbohydrates are esterified with fatty acids in the presence of polyether polyols.Type: GrantFiled: April 30, 1987Date of Patent: January 30, 1990Assignee: Huels AktiengesellschaftInventor: Peter Bickert
-
Patent number: 4892659Abstract: A separation agent essentially comprises an aliphatic or aromatic ester of a polysaccharide, except for cellulose acetate and an aromatic ester of cellulose. It is useful for separation of various chemical substances, especially optical resolution of optical isomers.Type: GrantFiled: July 27, 1988Date of Patent: January 9, 1990Assignee: Daicel Chemical Industries, Ltd.Inventors: Tohru Shibata, Hajime Namikoshi, Ichiro Okamoto