Plural Additional Oxygens Containing Patents (Class 554/109)
  • Publication number: 20150057373
    Abstract: 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: Application
    Filed: March 25, 2013
    Publication date: February 26, 2015
    Applicant: SIRNA THERAPEUTICS, INC
    Inventors: Matthew G. Stanton, Brian W. Budzik, Steven L. Colletti
  • Publication number: 20140309275
    Abstract: 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: Application
    Filed: September 27, 2012
    Publication date: October 16, 2014
    Inventors: Dennis C. Liotta, Jason Holt, JR., Michael G. Natchus, Mark T. Baillie, Eric J. Miller, Mary R. Galinski
  • Publication number: 20140275591
    Abstract: 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: Application
    Filed: March 14, 2013
    Publication date: September 18, 2014
    Applicant: Avanti Polar Lipids, Inc.
    Inventor: Avanti Polar Lipids, Inc.
  • Patent number: 8673816
    Abstract: 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: Grant
    Filed: May 5, 2010
    Date of Patent: March 18, 2014
    Assignees: Croda, Inc., Croda International PLC
    Inventors: Trevor Graham Blease, Gregory James Lindner, Lee David Richards
  • Publication number: 20140044661
    Abstract: 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: Application
    Filed: October 23, 2013
    Publication date: February 13, 2014
    Applicant: JOHNSON & JOHNSON CONSUMER COMPANIES, INC.
    Inventors: Michael J. Fevola, Frank C. Sun, Stacey E. York
  • Patent number: 8519170
    Abstract: 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: Grant
    Filed: May 10, 2012
    Date of Patent: August 27, 2013
    Assignee: Eisai R&D Management Co., Ltd.
    Inventors: Francis G. Fang, James E. Foy, Lynn Hawkins, Charles Lemelin, Andre Lescarbeau, Xiang Niu, Kuo-Ming Wu
  • Publication number: 20130059767
    Abstract: 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: Application
    Filed: May 28, 2010
    Publication date: March 7, 2013
    Applicant: COLGATE-PALMOLIVE COMPANY
    Inventors: Ravi Subramanyam, Charles J. Schramm, Aarti Rege
  • Publication number: 20120232298
    Abstract: 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: Application
    Filed: May 10, 2012
    Publication date: September 13, 2012
    Inventors: Francis G. Fang, James E. Foy, Lynn Hawkins, Charles Lemelin, Andre Lescarbeau, Xiang Niu, Kuo-Ming Wu
  • Publication number: 20120128530
    Abstract: 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: Application
    Filed: May 7, 2010
    Publication date: May 24, 2012
    Applicants: STEPAN UK LIMITED, M-I DRILLING FLUIDS UK LIMITED
    Inventors: Alyn Jenkins, Neil Grainger, Michael Blezard, Mathieu Pepin
  • Publication number: 20120114566
    Abstract: 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: Application
    Filed: January 9, 2012
    Publication date: May 10, 2012
    Applicants: 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
  • Publication number: 20120108550
    Abstract: 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: Application
    Filed: March 15, 2010
    Publication date: May 3, 2012
    Applicant: NEDERLANDSE ORGANISATIE VOOR TOEGEPAST- NATUURWETENSCHAPPELIJK ONDERZOEK TNO VK
    Inventors: 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
  • Publication number: 20120040834
    Abstract: 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: Application
    Filed: May 5, 2010
    Publication date: February 16, 2012
    Applicants: Croda International PLC, Croda, Inc.
    Inventors: Trevor Graham Blease, Gregory James Lindner, Lee David Richards
  • Publication number: 20120015960
    Abstract: 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: Application
    Filed: November 23, 2009
    Publication date: January 19, 2012
    Applicants: The Industry & Academic Cooperation in Chungnam National University, Pusan National University Industry-University Cooperation Foundation
    Inventors: Bum Joon Park, Nam Chul Ha, Sun Hye Lee, Gyu Yong Song, Jee Hyun Lee
  • Patent number: 8049023
    Abstract: 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: Grant
    Filed: November 15, 2010
    Date of Patent: November 1, 2011
    Assignee: Eisai R&D Management Co., Ltd.
    Inventors: Bruce DeCosta, Francis G. Fang, James E. Foy, Lynn Hawkins, Charles Lemelin, Xiang Niu, Kuo-Ming Wu
  • Publication number: 20110117125
    Abstract: 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: Application
    Filed: December 31, 2008
    Publication date: May 19, 2011
    Applicants: TEKMIRA PHARMACEUTICALS CORPORATION, THE UNIVERSITY OF BRITISH COLUMBIA, ALNYLAM PHARMACEUTICALS
    Inventors: 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
  • Publication number: 20110077302
    Abstract: 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: Application
    Filed: May 22, 2009
    Publication date: March 31, 2011
    Applicant: EVONIK GOLDSCHMIDT GMBH
    Inventors: Frank Hollmann, Oliver Thum, Christoph Toelle, Angelo Provinzano, Cornelis Gerrit Nijs Korevaar
  • Publication number: 20110060151
    Abstract: 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: Application
    Filed: November 15, 2010
    Publication date: March 10, 2011
    Applicant: EISAI R & D MANAGEMENT CO., LTD.
    Inventors: Bruce DECOSTA, Francis G. FANG, James E. FOY, Lynn HAWKINS, Charles LEMELIN, Xiang NIU, Kuo-Ming WU
  • Publication number: 20100256174
    Abstract: 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: Application
    Filed: November 20, 2008
    Publication date: October 7, 2010
    Inventors: Toshikazu Yamaguchi, Kenta Kawai, Katsuhiro Yamanaka, Noboru Tatsumi
  • Publication number: 20100233761
    Abstract: 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: Application
    Filed: March 10, 2010
    Publication date: September 16, 2010
    Inventors: Thomas J. Czartoski, Robert Perkins, Jorge L. Villanueva, Glenn Richards
  • Publication number: 20100063308
    Abstract: 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: Application
    Filed: November 12, 2009
    Publication date: March 11, 2010
    Inventors: Tongqian Chen, Chandra Vargeese, Kurt Vagle, Weimin Wang, Ye Zhang
  • Publication number: 20080145413
    Abstract: 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: Application
    Filed: December 19, 2006
    Publication date: June 19, 2008
    Inventors: Steffen Panzner, Christian Reinsch, Evgenios Siepi
  • Patent number: 6700006
    Abstract: 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: Grant
    Filed: April 10, 2001
    Date of Patent: March 2, 2004
    Assignee: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6696606
    Abstract: 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: Grant
    Filed: July 8, 2002
    Date of Patent: February 24, 2004
    Assignee: The Ohio State University Research Foundation
    Inventors: Robert W. Curley, Jr., Serena M. Mershon
  • Patent number: 6649780
    Abstract: 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: Grant
    Filed: December 17, 1999
    Date of Patent: November 18, 2003
    Assignees: Valentis, Inc., Max-Planck-Gesellschaft zur Foerderung der Wissaschaften B.V.
    Inventors: Hansjörg Eibl, Jinkang Wang, Yi Lin Zhang
  • Patent number: 6600059
    Abstract: 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: Grant
    Filed: January 10, 2002
    Date of Patent: July 29, 2003
    Assignee: Virginia Commonwealth University
    Inventors: Richard C. Franson, Raphael M. Ottenbrite
  • Patent number: 6503945
    Abstract: 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: Grant
    Filed: January 11, 2002
    Date of Patent: January 7, 2003
    Assignee: Council of Scientific & Industrial Research
    Inventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
  • Patent number: 6423855
    Abstract: 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: Grant
    Filed: January 12, 2000
    Date of Patent: July 23, 2002
    Assignee: Virginia Commonwealth University
    Inventors: Richard C. Franson, Raphael M. Ottenbrite
  • Patent number: 6346516
    Abstract: 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: Grant
    Filed: March 25, 1999
    Date of Patent: February 12, 2002
    Assignee: Council of Scientific & Industrial Research
    Inventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
  • Publication number: 20020007080
    Abstract: 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: Application
    Filed: April 10, 2001
    Publication date: January 17, 2002
    Applicant: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6333040
    Abstract: 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: Grant
    Filed: December 6, 1999
    Date of Patent: December 25, 2001
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Norbert Boyxen, Ansgar Behler, Hermann Hensen, Werner Seipel
  • Publication number: 20010031883
    Abstract: 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: Application
    Filed: April 10, 2001
    Publication date: October 18, 2001
    Applicant: The University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6271185
    Abstract: Industrial oils containing partial esters of triacylglycerol and triethanolamine or ethoxylated triethanolamine are described, as well as methods for making such oils.
    Type: Grant
    Filed: October 29, 1999
    Date of Patent: August 7, 2001
    Assignee: Cargill, Incorporated
    Inventors: Dharma Kodali, Scott C. Nivens
  • Patent number: 6235916
    Abstract: 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: Grant
    Filed: December 24, 1996
    Date of Patent: May 22, 2001
    Assignee: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6166232
    Abstract: 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: Grant
    Filed: December 8, 1998
    Date of Patent: December 26, 2000
    Assignee: Akzo Nobel NV
    Inventors: Manfred Bergfeld, Hartmut Ahrens, Axel Carstens
  • Patent number: 6072063
    Abstract: 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: Grant
    Filed: February 26, 1997
    Date of Patent: June 6, 2000
    Assignee: Clariant GmbH
    Inventors: Oliver Eyrisch, Rudolf Aigner
  • Patent number: 6031135
    Abstract: The invention relates to trimethylsphingosine derivatives which have some or all of the activities of the parent compound.
    Type: Grant
    Filed: May 13, 1996
    Date of Patent: February 29, 2000
    Assignee: Oncomembrane, Inc.
    Inventors: Fuqiang Ruan, Yasuyuki Igarashi, Sen-Itiroh Hakomori
  • Patent number: 6020489
    Abstract: 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: Grant
    Filed: March 18, 1997
    Date of Patent: February 1, 2000
    Assignee: Virginia Commonwealth University
    Inventors: Richard C. Franson, Raphael M. Ottenbrite
  • Patent number: 5962710
    Abstract: A method for preparing salicyloylamino acids is provided. An oligosalicylate and an amino acid are reacted to yield the salicyloylamino acid.
    Type: Grant
    Filed: May 9, 1997
    Date of Patent: October 5, 1999
    Assignee: Emisphere Technologies, Inc.
    Inventors: David Gschneidner, Doris O'Toole, John Freeman
  • Patent number: 5880299
    Abstract: 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: Grant
    Filed: October 24, 1996
    Date of Patent: March 9, 1999
    Assignee: Henkel Corporation
    Inventors: Oriol Ponsati Obiols, Nuria Bonastre, Joaquim Bigorra Llosas
  • Patent number: 5869715
    Abstract: 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: Grant
    Filed: September 27, 1995
    Date of Patent: February 9, 1999
    Assignee: The Reagents of the University of California
    Inventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam
  • Patent number: 5824812
    Abstract: 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: Grant
    Filed: September 17, 1996
    Date of Patent: October 20, 1998
    Assignee: The Regents of the University of California
    Inventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam, Alfred M. Aberle, Robert W. Malone
  • Patent number: 5783534
    Abstract: 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: Grant
    Filed: July 15, 1996
    Date of Patent: July 21, 1998
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Bernd Wahle, Joaquim Bigorra Llosas, Rafael Pi, Antoni Soler Codina, Emili Brau Balague, Yvonne Reichert, Peter Waltenberger
  • Patent number: 5705663
    Abstract: 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: Grant
    Filed: December 7, 1995
    Date of Patent: January 6, 1998
    Assignee: Servo Delden B.V.
    Inventors: Michael Brock, Meinolf Enneking, Kurt Kosswig
  • Patent number: 5696070
    Abstract: 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: Grant
    Filed: February 23, 1996
    Date of Patent: December 9, 1997
    Assignee: Kao Corporation
    Inventors: Osamu Tachizawa, Akira Sakaguchi, Tohru Katoh, Kohshiro Sotoya, deceased, Noriko Yamaguchi, Junichi Inokoshi, Muneo Aoyagi
  • Patent number: 5670677
    Abstract: 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: Grant
    Filed: September 18, 1995
    Date of Patent: September 23, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Oriol Ponsati Obiols, Joaquim Bigorra Llosas
  • Patent number: 5574179
    Abstract: 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: Grant
    Filed: February 28, 1995
    Date of Patent: November 12, 1996
    Assignee: The Procter & Gamble Company
    Inventors: 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
  • Patent number: 5525709
    Abstract: 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: Grant
    Filed: October 4, 1994
    Date of Patent: June 11, 1996
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Paul N. Davey, Brian J. Hardinge, Christopher P. Newman, Clive D. Richardson
  • Patent number: 5463094
    Abstract: 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: Grant
    Filed: May 23, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: David M. Brown, Erich M. Gatter, Cheryl A. Littau
  • Patent number: 5371252
    Abstract: 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: Grant
    Filed: November 10, 1992
    Date of Patent: December 6, 1994
    Assignee: L'Oreal
    Inventors: Alexandre Zysman, Henri Sebag
  • Patent number: 5292915
    Abstract: 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: Grant
    Filed: February 4, 1992
    Date of Patent: March 8, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Boettcher, Manfred Schwartz