Plural Additional Oxygens Containing Patents (Class 554/109)
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Publication number: 20150057373Abstract: Disclosed herein are novel cationic lipids that can be used in combination with other lipid components such as cholesterol and PEG-lipids to form lipid nanoparticles with oligonucleotides. The cationic lipids can demonstrate enhanced efficacy along with lower liver toxicity as a result of lower lipid levels in the liver. The present invention employs low molecular weight cationic lipids with one short lipid chain coupled with inclusion of hydrolysable functionality in the lipid chains to enhance the efficiency and tolerability of in vivo delivery of siRNA.Type: ApplicationFiled: March 25, 2013Publication date: February 26, 2015Applicant: SIRNA THERAPEUTICS, INCInventors: Matthew G. Stanton, Brian W. Budzik, Steven L. Colletti
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Publication number: 20140309275Abstract: The disclosure relates to compounds, pharmaceutical compositions, and methods of treating or preventing disease. In certain embodiments, the disclosure relates to methods of treating an infection or cancer comprising administering a pharmaceutical composition disclosed herein to a subject in need thereof. In a typical embodiment, one administers a pharmaceutical composition comprising sphingosine or a sphingosine analog to a subject at risk for, exhibiting symptoms of or diagnosed with a malaria infection.Type: ApplicationFiled: September 27, 2012Publication date: October 16, 2014Inventors: Dennis C. Liotta, Jason Holt, JR., Michael G. Natchus, Mark T. Baillie, Eric J. Miller, Mary R. Galinski
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Publication number: 20140275591Abstract: Disclosed are compounds of the general formula I and II (as further defined herein) are useful in the production of inhibitors of sphingolipid synthesis the production of sphingolipids. Suitable sphingolipids, include, but not limited to, sphingosine and compounds incorporating sphingosine or that may use sphingosine as an intermediate or a starting material in their synthesis (including, but not limited to, sphingosine-1-P, ceramide, gangliosides and sphingomyelin). In one contemplated use, compounds of the general formula I and II are useful in the production of sphingosine. In another contemplated use, compounds of the general formula I and II are useful in the production of a sphingofugin. Methods of manufacturing each of the above compounds are also provided.Type: ApplicationFiled: March 14, 2013Publication date: September 18, 2014Applicant: Avanti Polar Lipids, Inc.Inventor: Avanti Polar Lipids, Inc.
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Patent number: 8673816Abstract: Surfactant compounds which include an amine ended polyalkylene glycol hydrophile linked to C22 to C60 mainly hydrocarbyl, particularly composite hydrocarbyl, especially derived from a polymerised fatty acid and/or an aralkyl substituted phenol, hydrophobe, are useful in dispersing solids, particularly active agrochemicals, in aqueous media, or as adjuvants in agrochemical formulations, particularly of water soluble non-selective herbicides. In particular the hydrophobe is derived from polymerised fatty acids, such as dimer and, especially, trimer acids or from aralkyl substituted phenols. Aqueous dispersions using such surfactants can remain stable even with substantial concentrations of electrolyte e.g. in stable agrochemical dispersions including water soluble electrolyte agrochemical, such as glyphosate and/or ammonium sulphate.Type: GrantFiled: May 5, 2010Date of Patent: March 18, 2014Assignees: Croda, Inc., Croda International PLCInventors: Trevor Graham Blease, Gregory James Lindner, Lee David Richards
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Publication number: 20140044661Abstract: Provided are polyglyceryl compositions comprising one or more polyglyceryl compounds having: (a) a node structure comprising at least three contiguous glyceryl remnant units; (b) one or more cationic groups each linked to the node structure by an independently selected linking group; and (c) one or more hydrophobic moieties each independently (i) linked to the node structure by a linking group, or (ii) constituting a portion of one of the one or more cationic groups, wherein the composition has an average degree of polymerization determined by hydroxyl value testing (DPOH) of from about 3 to about 20. Also provided are polyglyceryl compounds which may compose such compositions, and uses of the polyglyceryl compositions and compounds.Type: ApplicationFiled: October 23, 2013Publication date: February 13, 2014Applicant: JOHNSON & JOHNSON CONSUMER COMPANIES, INC.Inventors: Michael J. Fevola, Frank C. Sun, Stacey E. York
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Patent number: 8519170Abstract: The present invention provides methods for preparing TLR-4 receptor agonist E6020: and stereoisomers thereof, which compounds are useful as an immunological adjuvants when co-administered with antigens such as vaccines for bacterial and viral diseases. Also provided are synthetic intermediates.Type: GrantFiled: May 10, 2012Date of Patent: August 27, 2013Assignee: Eisai R&D Management Co., Ltd.Inventors: Francis G. Fang, James E. Foy, Lynn Hawkins, Charles Lemelin, Andre Lescarbeau, Xiang Niu, Kuo-Ming Wu
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Publication number: 20130059767Abstract: A composition comprising an esterquat that is a quaternized reaction product of an alkanol amine and a fatty acid having a ratio of fatty acid to alkanol amine of 1.5 to 1.75, wherein 45 to 75% by weight of the fatty acids are saturated. Also, a method of softening a fabric and increasing fragrance delivery comprising treating the fabric with the composition.Type: ApplicationFiled: May 28, 2010Publication date: March 7, 2013Applicant: COLGATE-PALMOLIVE COMPANYInventors: Ravi Subramanyam, Charles J. Schramm, Aarti Rege
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Publication number: 20120232298Abstract: The present invention provides methods for preparing TLR-4 receptor agonist E6020: and stereoisomers thereof, which compounds are useful as an immunological adjuvants when co-administered with antigens such as vaccines for bacterial and viral diseases. Also provided are synthetic intermediates.Type: ApplicationFiled: May 10, 2012Publication date: September 13, 2012Inventors: Francis G. Fang, James E. Foy, Lynn Hawkins, Charles Lemelin, Andre Lescarbeau, Xiang Niu, Kuo-Ming Wu
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Publication number: 20120128530Abstract: The present invention relates to a corrosion inhibitor for use in the oil and gas exploration, recovery and processing industries. In particular, the invention relates to a quaternary ammonium compound suitable for use as such a corrosion inhibitor, to the manufacture of the quaternary ammonium compound, to compositions containing it, and to methods of using it. Quaternary ammonium compounds of the invention have the formula (I) in which R is C1-6 alkyl, C2-6 alkenyl, aryl, aralkyl; X, Y, and Z are each independently hydrogen, or R1CO—, provided that at least one of X, Y and Z is R1CO, where R1 is C5-23 alkyl or alkenyl containing 0, 1, 2 or 3 double bonds; D is C2-6 alkylene; E is C2-4 alkylene; p, q and r are each, independently, integers from 0 to 20, with the proviso that p+q+r is from 3 to 20; and A? is an anion.Type: ApplicationFiled: May 7, 2010Publication date: May 24, 2012Applicants: STEPAN UK LIMITED, M-I DRILLING FLUIDS UK LIMITEDInventors: Alyn Jenkins, Neil Grainger, Michael Blezard, Mathieu Pepin
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Publication number: 20120114566Abstract: This invention provides new lipoxin analogs, compositions containing analogs, and methods of using these compounds and compositions for treating and preventing oral inflammation, including gingivitis, periodontitis, and other forms of periodontal disease. The invention also provides for methods of treating and preventing oral inflammation, including gingivitis, periodontitis, and other forms of periodontal disease with compositions containing COX-2 inhibitors. Further, the invention provides methods for preventing systemic diseases beyond theoral cavity that are related to periodontal disease using the composition containing lipoxin analogs, COX-2 inhibitors, or both.Type: ApplicationFiled: January 9, 2012Publication date: May 10, 2012Applicants: TRUSTEES OF BOSTON UNIVERSITY, UNIVERSITY OF SOUTHERN CALIFORNIA, BRIGHAM AND WOMEN'S HOSPITAL, INC.Inventors: Thomas E. Van Dyke, Nicos A. Petasis, Charles N. Serhan
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Publication number: 20120108550Abstract: Use of polyunsaturated fatty acid derivatives as medicaments or functional foods. The present invention relates to the use of 1,2-fatty acid derivatives in the treatment or prevention of common diseases whose etiology is based on alterations (of any type) of the cell membrane lipids, for example, changes in levels, in the composition or in the structure of these lipids. In addition, for diseases in which the regulation of lipid composition and of the structure of the membranes (or proteins that interact with membranes) causes the reversion of pathological state.Type: ApplicationFiled: March 15, 2010Publication date: May 3, 2012Applicant: NEDERLANDSE ORGANISATIE VOOR TOEGEPAST- NATUURWETENSCHAPPELIJK ONDERZOEK TNO VKInventors: Pablo Vicente Escriba Ruiz, Xavier Busquets Xaubet, Silvia Teres Jimenez, Gwendolyn Barcelo Coblijn, Victoria Llado Canellas, Amaia Marcilla Etxenike, Maria Laura Martin, Monica Higuera Urbano, Rafael Alvarez Martinez, Daniel Horacio Lopez
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Publication number: 20120040834Abstract: Surfactant compounds which include an amine ended polyalkylene glycol hydrophile linked to C22 to C60 mainly hydrocarbyl, particularly composite hydrocarbyl, especially derived from a polymerised fatty acid and/or an aralkyl substituted phenol, hydrophobe, are useful in dispersing solids, particularly active agrochemicals, in aqueous media, or as adjuvants in agrochemical formulations, particularly of water soluble non-selective herbicides. In particular the hydrophobe is derived from polymerised fatty acids, such as dimer and, especially, trimer acids or from aralkyl substituted phenols. Aqueous dispersions using such surfactants can remain stable even with substantial concentrations of electrolyte e.g. in stable agrochemical dispersions including water soluble electrolyte agrochemical, such as glyphosate and/or ammonium sulphate.Type: ApplicationFiled: May 5, 2010Publication date: February 16, 2012Applicants: Croda International PLC, Croda, Inc.Inventors: Trevor Graham Blease, Gregory James Lindner, Lee David Richards
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Publication number: 20120015960Abstract: Provided are compounds for inhibiting Snail-p53 binding and therapeutic agents for cancer including the compounds as an effective component. The Snail-p53 binding inhibitors induce expression of p53 in K-Ras mutant cell lines, thereby enabling effective treatment or prevention of K-Ras mutant cancer, such as, pancreatic cancer, lung cancer, cholangioma, and colon cancer, of which diagnosis or treatment is not easy.Type: ApplicationFiled: November 23, 2009Publication date: January 19, 2012Applicants: The Industry & Academic Cooperation in Chungnam National University, Pusan National University Industry-University Cooperation FoundationInventors: Bum Joon Park, Nam Chul Ha, Sun Hye Lee, Gyu Yong Song, Jee Hyun Lee
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Patent number: 8049023Abstract: This invention relates to the synthesis for a precursor of E6020, compound 26, via a ?-keto amide alcohol intermediate, compound 22. The synthesis reacts compound 22 with compound 25 and the resultant intermediate is oxidized to produce compound 26, the precursor to E6020. Compounds 22 and 25, and their crystalline forms, represent separate embodiments of the invention. The invention also relates to compounds of formulas (3) and (4) and processes for their preparation. The ?-keto amide alcohol intermediate compound 22 is a compound of formula (3). Compound 25 is a compound of formula (4).Type: GrantFiled: November 15, 2010Date of Patent: November 1, 2011Assignee: Eisai R&D Management Co., Ltd.Inventors: Bruce DeCosta, Francis G. Fang, James E. Foy, Lynn Hawkins, Charles Lemelin, Xiang Niu, Kuo-Ming Wu
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Publication number: 20110117125Abstract: The present invention provides compositions and methods for the delivery of therapeutic agents to cells. In particular, these include novel lipids and nucleic acid-lipid particles that provide efficient encapsulation of nucleic acids and efficient delivery of the encapsulated nucleic acid to cells in vivo. The compositions of the present invention are highly potent, thereby allowing effective knock-down of specific target protein at relatively low doses. In addition, the compositions and methods of the present invention are less toxic and provide a greater therapeutic index compared to compositions and methods previously known in the art.Type: ApplicationFiled: December 31, 2008Publication date: May 19, 2011Applicants: TEKMIRA PHARMACEUTICALS CORPORATION, THE UNIVERSITY OF BRITISH COLUMBIA, ALNYLAM PHARMACEUTICALSInventors: Michael J. Hope, Sean C. Semple, Jianxin Chen, Thomas D. Madden, Barbara Mui, Pieter R. Cullis, Marco A. Ciufolini, Kim F. Wong, Muthiah Manoharan, Rajeev G. Kallanthottathil
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Publication number: 20110077302Abstract: The invention relates to the enzymatic synthesis of sphingolipids and compositions that contain sphingolipids from lysosphingolipids and carbonic esters, and to cosmetic, dermatological or pharmaceutical formulations containing said sphingolipids or compositions.Type: ApplicationFiled: May 22, 2009Publication date: March 31, 2011Applicant: EVONIK GOLDSCHMIDT GMBHInventors: Frank Hollmann, Oliver Thum, Christoph Toelle, Angelo Provinzano, Cornelis Gerrit Nijs Korevaar
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Publication number: 20110060151Abstract: This invention relates to the synthesis for a precursor of E6020, compound 26, via a ?-keto amide alcohol intermediate, compound 22. The synthesis reacts compound 22 with compound 25 and the resultant intermediate is oxidized to produce compound 26, the precursor to E6020. Compounds 22 and 25, and their crystalline forms, represent separate embodiments of the invention. The invention also relates to compounds of formulas (3) and (4) and processes for their preparation. The ?-keto amide alcohol intermediate compound 22 is a compound of formula (3). Compound 25 is a compound of formula (4).Type: ApplicationFiled: November 15, 2010Publication date: March 10, 2011Applicant: EISAI R & D MANAGEMENT CO., LTD.Inventors: Bruce DECOSTA, Francis G. FANG, James E. FOY, Lynn HAWKINS, Charles LEMELIN, Xiang NIU, Kuo-Ming WU
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Publication number: 20100256174Abstract: Disclosed is an external preparation composition having good transdermal absorbability. An external preparation composition having excellent transdermal absorbability can be produced by dissolving a medicinal substance or a salt thereof in a fatty acid-based ionic liquid to form a composite ionic composition of the medicinal substance. The external preparation composition can be used as a liquid preparation, an ointment, a cream, a plaster or the like, and enables to provide a preparation having excellent transdermal absorbability.Type: ApplicationFiled: November 20, 2008Publication date: October 7, 2010Inventors: Toshikazu Yamaguchi, Kenta Kawai, Katsuhiro Yamanaka, Noboru Tatsumi
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Publication number: 20100233761Abstract: A method of fractionating biomass, by permeability conditioning biomass suspended in a pH adjusted solution of at least one water-based polar solvent to form a conditioned biomass, intimately contacting the pH adjusted solution with at least one non-polar solvent, partitioning to obtain an non-polar solvent solution and a polar biomass solution, and recovering cell and cell derived products from the non-polar solvent solution and polar biomass solution. Products recovered from the above method. A method of operating a renewable and sustainable plant for growing and processing algae.Type: ApplicationFiled: March 10, 2010Publication date: September 16, 2010Inventors: Thomas J. Czartoski, Robert Perkins, Jorge L. Villanueva, Glenn Richards
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Publication number: 20100063308Abstract: The present invention relates to novel cationic lipids, transfection agents, microparticles, nanoparticles, and short interfering nucleic acid (siNA) molecules. The invention also features compositions, and methods of use for the study, diagnosis, and treatment of traits, diseases and conditions that respond to the modulation of gene expression and/or activity in a subject or organism. Specifically, the invention relates to novel cationic lipids, microparticles, nanoparticles and transfection agents that effectively transfect or deliver biologically active molecules, such as antibodies (e.g., monoclonal, chimeric, humanized etc.Type: ApplicationFiled: November 12, 2009Publication date: March 11, 2010Inventors: Tongqian Chen, Chandra Vargeese, Kurt Vagle, Weimin Wang, Ye Zhang
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Publication number: 20080145413Abstract: This disclosure describes structural elements that enhance fusogenicity of lipids and lipid assemblies (e.g. liposomes) with biological membranes, in particular cell membranes, and use of such structures. The elements are pH sensitive in terms of charge and hydrophilicity and undergo a polar—apolar transition when exposed to low pH.Type: ApplicationFiled: December 19, 2006Publication date: June 19, 2008Inventors: Steffen Panzner, Christian Reinsch, Evgenios Siepi
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Patent number: 6700006Abstract: Novel compounds derived from traditional semi- drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.Type: GrantFiled: April 10, 2001Date of Patent: March 2, 2004Assignee: University of Southern MississippiInventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
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Patent number: 6696606Abstract: A solid phase synthetic method for preparing arylretinamides is provided. The method comprises reacting hexachloroacetone with a solvent-suspended resin-bound triphenylphosphine to provide a suspension comprising an activated chlorinating reagent; reacting retinoic acid with the activated chlorinating reagent to provide retinoyl chloride; adding pyridine and a select arylamine to the resulting mixture; and stirring the resulting mixture for a time and at a temperature sufficient for the select arylamine to react with the retinoyl chloride and provide the arylretinamide. Also provided, are select arylretinamides that can be prepared by the present method, and methods of using such arylretinamides to induce apoptosis in cancer cells.Type: GrantFiled: July 8, 2002Date of Patent: February 24, 2004Assignee: The Ohio State University Research FoundationInventors: Robert W. Curley, Jr., Serena M. Mershon
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Patent number: 6649780Abstract: Cationic lipids are provided which are useful in the preparation of liposomes and other lipid vesicle carriers. The lipids of the invention are particularly useful as carriers of nucleic acids and other negatively charged substances, for delivery to cells.Type: GrantFiled: December 17, 1999Date of Patent: November 18, 2003Assignees: Valentis, Inc., Max-Planck-Gesellschaft zur Foerderung der Wissaschaften B.V.Inventors: Hansjörg Eibl, Jinkang Wang, Yi Lin Zhang
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Patent number: 6600059Abstract: The present invention provides compositions and methods for protecting cells from injury due to intrinsic membrane lysis, oxidation and/or invasion by destructive agents. Even more particularly, the present invention provides compositions and methods for treating or prophylactically inhibiting phospholipase mediated injury, injury due to oxidation, and inflammation. In a very specific sense, this invention provides compositions and methods of making these compositions that are inhibitors of phospholipase.Type: GrantFiled: January 10, 2002Date of Patent: July 29, 2003Assignee: Virginia Commonwealth UniversityInventors: Richard C. Franson, Raphael M. Ottenbrite
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Patent number: 6503945Abstract: The present invention provides novel cationic amphiphiles containing novel N-hydroxyalkyl group and therapeutic formulations containing the said amphiphiles that are capable of facilitating transport of biologically active molecules into cells.Type: GrantFiled: January 11, 2002Date of Patent: January 7, 2003Assignee: Council of Scientific & Industrial ResearchInventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
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Patent number: 6423855Abstract: The present invention provides compositions and methods for protecting cells from injury due to intrinsic membrane lysis, oxidation and/or invasion by destructive agents. Even more particularly, the present invention provides compositions and methods for treating or prophylactically inhibiting phospholipase mediated injury, injury due to oxidation, and inflammation. In a very specific sense, this invention provides compositions and methods of making these compositions that are inhibitors of phospholipase.Type: GrantFiled: January 12, 2000Date of Patent: July 23, 2002Assignee: Virginia Commonwealth UniversityInventors: Richard C. Franson, Raphael M. Ottenbrite
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Patent number: 6346516Abstract: The present invention provides novel cationic amphiphiles containing novel N-hydroxyalkyl group and therapeutic formulations containing the said amphiphiles that are capable of facilitating transport of biologically active molecules into cells.Type: GrantFiled: March 25, 1999Date of Patent: February 12, 2002Assignee: Council of Scientific & Industrial ResearchInventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
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Publication number: 20020007080Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.Type: ApplicationFiled: April 10, 2001Publication date: January 17, 2002Applicant: University of Southern MississippiInventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
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Patent number: 6333040Abstract: Compositions having refatting properties for use in and as cosmetic preparations wherein the compositions contain (a) monoglyceride (ether) sulfates, and (b) fatty acid partial glycerides; and processes for their preparation.Type: GrantFiled: December 6, 1999Date of Patent: December 25, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Norbert Boyxen, Ansgar Behler, Hermann Hensen, Werner Seipel
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Publication number: 20010031883Abstract: Novel compounds derived from traditional semi- drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.Type: ApplicationFiled: April 10, 2001Publication date: October 18, 2001Applicant: The University of Southern MississippiInventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
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Patent number: 6271185Abstract: Industrial oils containing partial esters of triacylglycerol and triethanolamine or ethoxylated triethanolamine are described, as well as methods for making such oils.Type: GrantFiled: October 29, 1999Date of Patent: August 7, 2001Assignee: Cargill, IncorporatedInventors: Dharma Kodali, Scott C. Nivens
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Patent number: 6235916Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.Type: GrantFiled: December 24, 1996Date of Patent: May 22, 2001Assignee: University of Southern MississippiInventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
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Patent number: 6166232Abstract: A process is described for producing ester quats of the formula (I) ##STR1## where X.sup.- is an anion of an inorganic or organic acid, R.sub.a is a C.sub.1 to C.sub.4 alkyl group, R.sub.b and R.sub.c are each, independently of one another, a C.sub.1 to C.sub.3 alkylene group, and R.sub.d is a C.sub.1 to C.sub.22 fragment of a saturated and/or unsaturated aliphatic carboxylic acid, m, n, p, and q are integers, m has a value from 1 to 3, n a value from 0 to 3, p a value from 0 to 1, m+n+p=4, and q has the value 1 or, if m=3, n=0, and p=1, the value 2, in which process a quaternary compound of the formula (II) ##STR2## where X.sup.-, R.sub.a, R.sub.b, R.sub.c, m, n, p, and q have the above meanings, is esterified, in the presence of an oxo acid of phosphorus and/or one of its alkali or alkaline-earth salts as a catalyst, with a saturated and/or unsaturated C.sub.1 to C.sub.22 carboxylic acid, alone or in a mixture, while withdrawing water.Type: GrantFiled: December 8, 1998Date of Patent: December 26, 2000Assignee: Akzo Nobel NVInventors: Manfred Bergfeld, Hartmut Ahrens, Axel Carstens
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Patent number: 6072063Abstract: Ester quats of the formula (1) below are described: ##STR1## where RCO is an aliphatic acyl radical having 6 to 22 carbon atoms, R.sup.1 is a methyl radical, R.sup.2 is a C.sub.1 -C.sub.6 -alkyl radical, R.sup.3 is a C.sub.3 -C.sub.6 -alkyl radical and X.sup.- is a halogen anion. They are prepared by quaternizing the corresponding carboxylic acid ethanolamine ester compound with a methyl halide in the absence or presence of solvents. The ester quats of the invention have a low melting point. Furthermore, even in high concentration they are highly water soluble and, on account of their preparation, are obtained in high purity and free from toxic contents. These ester quats can be used in many ways and are suitable, for example, for preparing solid or aqueous formulations having a high surfactant effect.Type: GrantFiled: February 26, 1997Date of Patent: June 6, 2000Assignee: Clariant GmbHInventors: Oliver Eyrisch, Rudolf Aigner
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Patent number: 6031135Abstract: The invention relates to trimethylsphingosine derivatives which have some or all of the activities of the parent compound.Type: GrantFiled: May 13, 1996Date of Patent: February 29, 2000Assignee: Oncomembrane, Inc.Inventors: Fuqiang Ruan, Yasuyuki Igarashi, Sen-Itiroh Hakomori
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Patent number: 6020489Abstract: Water or lipid soluble, pharmacologically active, antioxidant, anti-phospholipase compounds that are chemically defined. The compounds protect mammalian cells by inhibiting PLA.sub.2 and preventing oxidation. In particular, each compound has at least two fatty moieties and no active hydroxy group. The compound may also have at least one ionizable group, which may be a carboxyl group, and each of the fatty moieties has from sixteen to twenty carbon atoms and at least one cis-unsaturated double bond.Type: GrantFiled: March 18, 1997Date of Patent: February 1, 2000Assignee: Virginia Commonwealth UniversityInventors: Richard C. Franson, Raphael M. Ottenbrite
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Patent number: 5962710Abstract: A method for preparing salicyloylamino acids is provided. An oligosalicylate and an amino acid are reacted to yield the salicyloylamino acid.Type: GrantFiled: May 9, 1997Date of Patent: October 5, 1999Assignee: Emisphere Technologies, Inc.Inventors: David Gschneidner, Doris O'Toole, John Freeman
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Patent number: 5880299Abstract: The invention relates to new esterquats which are obtained by reacting trialkanolamines with a mixture of fatty acids and dicarboxylic acids and quaternizing the resulting esters in known manner, optionally after alkoxylation. Cationic surfactants are obtained which show particularly high ecotoxicological compatibility, provide synthetic and natural fibers with a pleasant feel and, at the same time, reduce electrostatic charging between the filaments.Type: GrantFiled: October 24, 1996Date of Patent: March 9, 1999Assignee: Henkel CorporationInventors: Oriol Ponsati Obiols, Nuria Bonastre, Joaquim Bigorra Llosas
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Patent number: 5869715Abstract: For use in transporting biologically active species into and through membrane barriers, a cationic amine compound is utilized that has the general structure: ##STR1## wherein R.sub.4 and R.sub.5 are a pair of same or different lipoyl moieties selected from a group consisting of an alkyl, alkenyl, alkynyl, alkanoyl, alkenoyl, or alkynoyl groups and for R.sub.1 R.sub.2, and R.sub.3 at least two are hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl groups or at least one amine bonded halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group or a mixture of at least one halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group and at least one hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl group, and X.sup.- is an anion.Type: GrantFiled: September 27, 1995Date of Patent: February 9, 1999Assignee: The Reagents of the University of CaliforniaInventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam
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Patent number: 5824812Abstract: Amine containing compounds and their use in the generation of cytofectin:polynucleotide complexes for transfection of cells, formulations, counterions, and reaction conditions for maximizing the transfection include using cationic amine compounds that have the general structure: ##STR1## wherein R.sub.4 and R.sub.5 are a pair of same or different lipoyl moieties selected from a group consisting of an alkyl, alkenyl, alkynyl, alkanoyl, alkenoyl, or alkynoyl groups and for R.sub.1, R.sub.2, and R.sub.3 at least two are hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl groups or at least one amine bonded halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group or a mixture of at least one halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group and at least one hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl group, and X.sup.Type: GrantFiled: September 17, 1996Date of Patent: October 20, 1998Assignee: The Regents of the University of CaliforniaInventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam, Alfred M. Aberle, Robert W. Malone
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Patent number: 5783534Abstract: A process for the production of a solid esterquat free from solvents comprising the steps ofA) forming a mixture comprising(i) at least one fatty acid triethanolamine ester corresponding to formula (I) ##STR1## in which R.sup.1 CO is a saturated and/or unsaturated acyl radical containing 6 to 22 carbon atoms, R.sup.2 and R.sup.3 independently of one another represent hydrogen or have the same meaning as R.sup.1 CO, and n, m and p together stand for O or for a number of from 1 to 10;(ii) at least one fatty alcohol polyglycol ether, and(iii) at least one fatty acid partial glyceride; andB) adding an alkylating agent to the above mixture to form said solid esterquat.Type: GrantFiled: July 15, 1996Date of Patent: July 21, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bernd Wahle, Joaquim Bigorra Llosas, Rafael Pi, Antoni Soler Codina, Emili Brau Balague, Yvonne Reichert, Peter Waltenberger
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Patent number: 5705663Abstract: The invention relates to quaternized triethanolamine difatty acid esters prepared from triethanolamine, fatty acid, fatty acid ester and a quaternizing agent and to a process for their preparation and to their use. The quaternized triethanolamine difatty acid esters thus prepared can be used to produce particularly storage-, temperature- and viscosity-stable rinse cycle laundry softeners having a high active content.Type: GrantFiled: December 7, 1995Date of Patent: January 6, 1998Assignee: Servo Delden B.V.Inventors: Michael Brock, Meinolf Enneking, Kurt Kosswig
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Patent number: 5696070Abstract: A liquid softener composition comprising a quaternary ammonium salt represented by the general formula (1) and a method for its preparation: ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are an alkyl group or hydroxyalkyl group of 1 to 4 carbon atoms, R.sup.4 and R.sup.5 are an unsubstituted or hydroxyl group-substituted linear or branched alkyl group or alkenyl group of 8 to 36 carbon atoms, A is a linear or branched alkylene group of 2 or 3 carbon atoms, X is an anion group, n is an integer in the range of 1 to 6, and m is a numeral in the range of 0 to 20.Type: GrantFiled: February 23, 1996Date of Patent: December 9, 1997Assignee: Kao CorporationInventors: Osamu Tachizawa, Akira Sakaguchi, Tohru Katoh, Kohshiro Sotoya, deceased, Noriko Yamaguchi, Junichi Inokoshi, Muneo Aoyagi
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Patent number: 5670677Abstract: A process for the production of color- and odor-stable quaternized fatty acid triethanolamine ester salts comprising the steps ofA) partially or fully esterifying triethanolamine with at least one fatty acid in the presence of hypophosphorous acid;B) adding a peroxide compound and an alkali metal boranate to the esterification product from step A); andC) quaternizing the esterification product with an alkyl halide, a (di)alkyl sulfate or an alkylene oxide in the presence of a phenol derivative and a hydroxycarboxylic acid.Type: GrantFiled: September 18, 1995Date of Patent: September 23, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Oriol Ponsati Obiols, Joaquim Bigorra Llosas
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Patent number: 5574179Abstract: The present invention relates to softening compounds; stable, homogeneous, preferably concentrated, aqueous liquid and solid textile treatment compositions; and intermediate compositions and/or processes for making said compositions.The compositions of the present invention contain diester quaternary ammonium compounds wherein the fatty acyl groups have an Iodine Value of from greater than about 5 to less than about 100, a cis/trans isomer weight ratio of greater than about 30/70 when the Iodine Value is less than about 25, the level of unsaturation being less than about 65% by weight, wherein said compounds are capable of forming concentrated aqueous compositions with concentrations greater than about 13% by weight at an Iodine Value of greater than about 10 without viscosity modifiers other than normal polar organic solvents present in the raw material of the compound or added electrolyte.Type: GrantFiled: February 28, 1995Date of Patent: November 12, 1996Assignee: The Procter & Gamble CompanyInventors: Errol H. Wahl, Dennis R. Bacon, Ellen S. Baker, Jean-Francois Bodet, Michael E. Burns, Hugo J. M. Demeyere, Charles A. Hensley, Robert Mermelstein, John C. Severns, John H. Shaw, Jr., Michael P. Siklosi, Alice M. Vogel, Jeffrey W. Watson
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Patent number: 5525709Abstract: The invention relates to the preparation of ceramides by a two step process involving conversion of a 2-hydroximino-3-oxo-alkanoate into a 2-alkanoylamido-3-oxo-alkanoate intermediate by acylation of the oxime and reduction of the oxime ester group to an amido group, followed by reduction of the keto and ester group of the intermediate to the 1,3 diol of the ceramide. The oxime acylation and the first reduction may be carried out consecutively or simultaneously. The first reduction is preferably a catalytic hydrogenation and the second reduction is preferably a borohydride reduction.The invention further relates to novel 2-alkanoylamido-3-oxo-alkanoates and 2-alkanoyloximino-3-oxo-alkanoates which are useful as intermediates for conversion into ceramides.Type: GrantFiled: October 4, 1994Date of Patent: June 11, 1996Assignee: Unilever Patent Holdings B.V.Inventors: Paul N. Davey, Brian J. Hardinge, Christopher P. Newman, Clive D. Richardson
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Patent number: 5463094Abstract: A process for a high temperature, solvent free quaternization of certain tertiary amines using dimethylsulfate to produce quaternary ammonium methyl sulfates which may be used in fabric softening and other applications, is disclosed.Type: GrantFiled: May 23, 1994Date of Patent: October 31, 1995Assignee: Hoechst Celanese CorporationInventors: David M. Brown, Erich M. Gatter, Cheryl A. Littau
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Patent number: 5371252Abstract: A compound of the formula:R--NHCOOCH(CH.sub.2 OCH.sub.2 CHOHCH.sub.2 OH).sub.2 (I)wherein R is a C.sub.10 -C.sub.20 alkyl, optionally unsaturated, is employed in the preparation of wax microdispersions useful particularly in cosmetic composition for the hair.Type: GrantFiled: November 10, 1992Date of Patent: December 6, 1994Assignee: L'OrealInventors: Alexandre Zysman, Henri Sebag
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Patent number: 5292915Abstract: The invention relates to compounds containing carbonate groups and carbonyl groups and having the general formula ##STR1## in which R stands for a C.sub.1 -C.sub.4 -alkyl radical, an aryl radical, or a radical R.sup.1, whereR.sup.1 has the following formula ##STR2## in which R.sup.2 to R.sup.6 stand for H, alkyl, OH, O-alkyl, SH, S-alkyl, halogen, N(alkyl).sub.2, or N(alkyl)(aryl) and at least one but not more than three of the radicals R.sup.2 to R.sup.6 stand for a radical of the formula ##STR3## in which A, B and C stand for alkylene, cycloalkylene, oxaalkylene, polyoxaalkylene or arylene, k and l both stand for an integer from 1 to 80, and the end group Z stands for alkyl, aryl, alkoxycarbonyl, alkoxycarbonyloxy, or aryl.These compounds are suitable for use as emulsifiers for dispersions.Type: GrantFiled: February 4, 1992Date of Patent: March 8, 1994Assignee: BASF AktiengesellschaftInventors: Andreas Boettcher, Manfred Schwartz