Another Reactant Is A Carboxylic Acid Anhydride (i.e., Contains -c(=o)-o-c(=o)-) Patents (Class 554/164)
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Patent number: 10292929Abstract: Described herein is a silicone replacement for use in a personal care formulation comprising a mixture of at least one polymeric ester and at least one non-polymeric ester. The polymeric ester is an esterification reaction product of (i) at least one first dicarboxylic acid, (ii) at least one first monofunctional alcohol or monofunctional carboxylic acid and (iii) glycerin or derivatives thereof. The non-polymeric ester is an esterification reaction product of (i) at least one second dicarboxylic acid and (ii) at least one second monofunctional alcohol, wherein the replacement is substantially free of silicone. As described is a personal care formulation that is substantially free of silicone, wherein the formulation comprises a silicone replacement consisting substantially of a mixture of at least one polymeric ester as described above, and a non-polymeric ester as described above. Related methods are also described.Type: GrantFiled: March 23, 2017Date of Patent: May 21, 2019Inventors: Rocco Burgo, Daniel Winn, Kimberly Burch
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Patent number: 9610237Abstract: Described herein is a silicone replacement for use in a personal care formulation comprising a mixture of at least one polymeric ester and at least one non-polymeric ester. The polymeric ester is an esterification reaction product of (i) at least one first dicarboxylic acid, (ii) at least one first monofunctional alcohol or monofunctional carboxylic acid and (iii) glycerin or derivatives thereof. The non-polymeric ester is an esterification reaction product of (i) at least one second dicarboxylic acid and (ii) at least one second monofunctional alcohol, wherein the replacement is substantially free of silicone. As described is a personal care formulation that is substantially free of silicone, wherein the formulation comprises a silicone replacement consisting substantially of a mixture of at least one polymeric ester as described above, and a non-polymeric ester as described above. Related methods are also described.Type: GrantFiled: May 13, 2014Date of Patent: April 4, 2017Assignee: Inolex Investment CorporationInventors: Rocco Burgo, Daniel Winn, Kimberly Burch
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Patent number: 9334358Abstract: Novel polyglycerol oligoesters derived from reaction of polyglycerol with a mixture of mono and diacids and also combinations of these novel polyglycerol oligoesters with known polyol monoesters, particularly known polyglycerol monoesters are disclosed. The use of these novel polyglycerol oligoesters and combination of esters as emulsifiers, solubilisers and/or thickeners especially in personal care formulations is also disclosed.Type: GrantFiled: July 13, 2011Date of Patent: May 10, 2016Assignee: CRODA INTERNATIONAL PLCInventors: Sean Philip Nigel Rouse, James Richard Humphrey, Ben Cale, David Freeman, Alun Barnes
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Publication number: 20150073078Abstract: A process can prepare a compound having the formula wherein R1, R2 and R3 are independently selected from hydrogen and acyl groups, wherein at least one of R1, R2 and R3 is a branched chain long acyl group including 2, 4 or 6 branched acyl groups wherein at least one of R1, R2 and R3 is selected from short acyl groups of the formula wherein q is from 0 to 4.Type: ApplicationFiled: September 15, 2014Publication date: March 12, 2015Inventors: Lars Wiebe, Thomas Schmidt
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Publication number: 20120058232Abstract: The present invention provides a method for the preparation of diacetyl tartaric acid esters of mono- and di-glycerides, which comprises steps of: adding L-tartaric acid and/or DL-tartaric acid and acetic anhydride into a reaction kettle, adding concentrated phosphoric acid as catalyst and mixing together to form a reaction system; heating the reaction kettle until a temperature of the reaction system reaches 50° C.˜55° C. to initiate a reaction, after the temperature of the reaction system rises and then drops to 80° C.˜90° C., keeping the temperature at 80° C.˜90° C. for 20˜60 min to obtain an intermediate product; adding stearic acid esters of mono- and di-glycerides to the intermediate product, then adding powdery sodium hydroxide as catalyst, controlling an inner pressure of the reaction kettle at ?0.09 Mpa˜?0.098 Mpa, heating the reaction kettle again until a temperature of the reaction system reaches 90° C.˜130° C., and keeping the temperature at 90° C.˜130° C.Type: ApplicationFiled: September 27, 2010Publication date: March 8, 2012Inventors: Gaofeng Liu, Shuming Yu
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Patent number: 8119824Abstract: As means for producing a biodiesel oil from a feed oil containing a free fatty acid at high efficiency, the following processes (1) to (3) are provided: (1) a process for producing a higher fatty acid ester, comprising reacting a lower alcohol with a higher fatty acid in the presence of an amorphous carbon having a sulfonate group introduced therein, thereby producing the higher fatty acid ester; (2) a process for producing a higher fatty acid ester, comprising reacting a lower alcohol with a higher fatty acid and a higher fatty acid triglyceride in the presence of an amorphous carbon having a sulfonate group introduced therein, thereby producing the higher fatty acid ester by both of the reaction between the lower alcohol and the higher fatty acid and the reaction between the lower alcohol and the higher fatty acid triglyceride; and (3) a process for producing a higher fatty acid ester, comprising: reacting a lower alcohol with a higher fatty acid and a higher fatty acid triglyceride in the presence of an amType: GrantFiled: June 20, 2006Date of Patent: February 21, 2012Assignee: Tokyo Institute of TechnologyInventor: Michikazu Hara
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Patent number: 7754904Abstract: A process is described in which an unsaturated fat is reacted in a homometathesis reaction in the presence of at least one non-aqueous ionic liquid to produce both an olefinic fraction and a composition of monoalcohol diesters or diacids. Particular application to a mixture of esters of an oleic sunflower seed oil or an oleic rapeseed oil, the process producing both an olefinic fraction and a composition of monoalcohol diesters or diacids wherein, in general, more than half of its chains is constituted by unsaturated C18 chains.Type: GrantFiled: January 23, 2007Date of Patent: July 13, 2010Assignee: Institut Francais du PetroleInventors: Hélène Olivier-Bourbigou, Gérard Hillion, Christophe Vallee
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Patent number: 6583302Abstract: Triglyceride oils having unsaturated fatty acid substituents are modified to convert sites of unsaturation to C-2 to C-10 diesters. The resulting derivatives are characterized by thermal and oxidative stability, have low temperature performance properties and are environmentally-friendly. They have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids. The triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction.Type: GrantFiled: January 25, 2002Date of Patent: June 24, 2003Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu
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Patent number: 6515154Abstract: The present invention relates to acetoacetic acid derivatives of the formula Ia or Ib, to processes for their preparation and to their use for the preparation of 2,15-hexadecanedione. The invention further relates to the use of the compounds of the formula Ia or Ib where R is an optionally substituted straight-chain or branched C1-C6-alkyl, C1-C6-alkoxyalkyl or phenyl radical, alkoxy groups are a combination of an alkyl group according to the above definition with an oxygen atom, e.g. methoxy, ethoxy, propoxy, butoxy or pentoxy groups, which comprises adding an acetoacetic ester of the formula II to 1,9-decadiene by a free-radical means, as intermediate for the preparation of muscone (3-methylcyclopentadecanone).Type: GrantFiled: May 3, 2001Date of Patent: February 4, 2003Assignee: BASF AktiengesellschaftInventor: Klaus Ebel
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Patent number: 6225485Abstract: What is shown is a high purity adduct of castor oil and a cyclic carboxylic acid anhydride, charactered by the absence of free acid anhydride, which is used in personal care products. The adduct is made by a process, without side reactions, which includes (a) reacting castor oil and cyclic carboxylic acid anhydride at a temperature of 75-120° C. for 4 to 24 hours, and then (b) continuing the reaction at room temperature for at least 1 week to react any remaining maleic anhydride. Skin and hair care formulations of such adducts are also described.Type: GrantFiled: June 29, 1999Date of Patent: May 1, 2001Assignee: ISP Investments Inc.Inventors: Steven H. Bertz, Frank M. Miksza, Elliott Zucker
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Patent number: 5668244Abstract: A liquid polyester obtained by reacting a cyclic acid anhydride (A) containing at least 10 mol % of one of specific cyclic acid anhydrides with an epoxy compound (B) in a cyclic acid anhydride (A):epoxy compound (B) molar ratio of 10:8-10:12, can be applied with a conventionally generally used film-forming machine such as a roll coater or a printing machine, can easily give a film-forming material such as a solvent-free coating composition or ink and a curable liquid resin for use as an adhesive, is a low-temperature curing liquid polyester useful as a compatibilizer, a surface-tension modifier, a pigment dispersing agent and a metal chelating agent, and is curable in air in the presence of a relatively small amount of a catalyst.Type: GrantFiled: June 16, 1995Date of Patent: September 16, 1997Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Miki Kawashima, Takeo Yamaguchi, Kunio Horiuchi, Hiromi Uchida
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Patent number: 5536856Abstract: Esterification is carried out in a column reactor (14) in which there is a plurality of esterification trays (15) each having predetermined liquid hold-up and containing a charge of a solid esterification catalyst thereon. e.g. an ion exchange resin containing a --SO.sub.3 H and/or --COOH groups. A liquid phase containing the carboxylic acid component, e.g. a fatty acid mixture, flows down the column reactor from one esterification tray to the next downward one against an upflowing alcohol vapour stream, e.g. methanol vapour. Relatively dry alcohol vapour is injected (21) into the bottom of the column reactor. Water of esterification is removed from the top of the column reactor in the vapour stream (26), whilst ester product is recovered (23) from the sump of the reactor. As the liquid flows down the trays it encounters progressively drier alocohol and the esterification equilibrium reaction is driven further and further towards 100% ester formation.Type: GrantFiled: February 23, 1994Date of Patent: July 16, 1996Assignee: Davy Process Technology LimitedInventors: George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
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Patent number: 5387705Abstract: A fast, three-stage, low temperature process for the conversion of fatty acids into food grade-anhydrides is disclosed. The process comprises as a first step the reaction of a higher fatty acid with a dehydrating agent under mild conditions. A second process step comprises the further conversion of mixed anhydrides to symmetrical anhydrides by continuous removal of the dehydrating agent and by-product acid from the reaction mixture under vacuum. In a third process step, the symmetrical anhydrides are purified under mild conditions, preferably using thin-film short path evaporation. The resulting anhydrides have minimal by-products and good color and odor.Type: GrantFiled: August 13, 1993Date of Patent: February 7, 1995Assignee: The Procter & Gamble CompanyInventors: Gordon K. Stipp, Bernard W. Kluesener
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Patent number: 5362894Abstract: A method of obtaining a fatty acid-esterified alkoxylated polyol useful as a reduced calorie fat substitute is provided. The method utilizes a C.sub.1 -C.sub.4 alkyl ester of a C.sub.8 -C.sub.24 fatty acid such as methyl stearate or methyl oleate and a short chain acid-esterified alkoxylated polyol such as the acetate of propoxylated glycerin as reactants.Type: GrantFiled: November 12, 1993Date of Patent: November 8, 1994Assignees: Arco Chemical Technology, L.P., CPC International, Inc.Inventors: Beth M. Handwerker, Charles F. Cooper, Bernard C. Sekula
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Patent number: 5288884Abstract: A convenient method of obtaining a reduced calorie esterified alkoxylated polyol containing both long chain saturated linear acyl groups and shorter chain unsaturated acyl groups is provided.Type: GrantFiled: October 22, 1992Date of Patent: February 22, 1994Assignees: Arco Chemical Technology, L.P., CPC International, Inc.Inventor: Charles F. Cooper
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Patent number: 5175323Abstract: A novel method is provided for the preparation of food grade esterified propoxylated glycerin by transesterification in a solventless system by reacting at temperatures of from about 100.degree. C. to about 250.degree. C. a propoxylated glycerin having from 2 to 100 oxypropylene units per glycerin with a saturated or unsaturated C10 to C24 fatty acid ester or mixtures thereof.Type: GrantFiled: August 1, 1988Date of Patent: December 29, 1992Assignee: Arco Chemical Technology, L.P.Inventor: Charles F. Cooper
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Patent number: 5164191Abstract: The present invention features a method of making lipid vesicles and the lipid vesicles themselves made from monomeric and dimeric alkyds. These alkyds are esters made as a condensation product of a first reactant having at least one free hydroxyl group and a C.sub.12 -C.sub.20 fatty acids chain and a second reactant which is an aromatic acid chloride or anhydride. Preferred first reactants are esters of polyols and C.sub.12 -C.sub.20 fatty acids, ethers of polyols and C.sub.12 -C.sub.20 fatty acids, and C.sub.12 -C.sub.20 fatty alcohols.Type: GrantFiled: February 12, 1991Date of Patent: November 17, 1992Assignee: Micro Vesicular Systems, Inc.Inventors: S. Esmail Tabibi, An-Cheng Chang, Rajiv Mathur, Donald F. H. Wallach
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Patent number: RE42313Abstract: Triglyceride oils having unsaturated fatty acid substituents are modified to convert sites of unsaturation to C-2 to C-10 diesters. The resulting derivatives are characterized by thermal and oxidative stability, have low temperature performance properties and are environmentally-friendly. They have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids. The triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction.Type: GrantFiled: June 7, 2005Date of Patent: April 26, 2011Assignees: The United States of America as repesented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu