Amidation Patents (Class 554/69)
  • Patent number: 5571934
    Abstract: Process for preparing solutions of polyhydroxy-fatty acid amides having good color qualityIn the process described, at least one sulfur compound from the group of dithionous acid is added in an active amount to the crude solutions, which are in general more or less brown in color, after which water-clear polyhydroxy-fatty acid amide products result.
    Type: Grant
    Filed: August 1, 1995
    Date of Patent: November 5, 1996
    Assignee: Hoechst AG
    Inventors: Bernd Papenfuhs, Reinhard Vybiral
  • Patent number: 5565590
    Abstract: This invention relates to a process for recycling waste material selected from amino-carboxylic acid oligomers or polymers and amido-carboxylic acid oligomers or polymers into amido-carboxylic acids. A mixture containing water, an oligomeric or polymeric waste material, and a carboxylic acid is heated. The mixture is cooled to obtain a two phase system containing an aqueous phase and an organic phase which are separated. Carboxylic acids, unreacted starting materials, and the monomeric amido-carboxylic acid product are distilled from the organic phase. The remaining solid residue composed of high boiling oligomeric amino-carboxylic acids is recycled into Step (A).
    Type: Grant
    Filed: November 7, 1994
    Date of Patent: October 15, 1996
    Assignee: Eastman Chemical Company
    Inventors: George C. Zima, Gary P. Lutz, Gary W. McChesney, T. Hugh Williams
  • Patent number: 5539134
    Abstract: The preparation von N-alkanoyl-polyhydroxyalkylamines I in which ##STR1## in which Z stands for the polyhydroxyalkyl radical of a monosaccharide or oligosaccharide,R.sup.1 denotes hydrogen or C.sub.1 -C.sub.8 alkyl andR.sup.2 denotes C.sub.1 -C.sub.21 alkyl, by the reaction of polyhydroxyalkylamines of the general formula IIZ--NH--R.sup.1 (II),with alkyl carboxylates of the general formula III ##STR2## in which R.sup.3 denotes a C.sub.1 -C.sub.4 alkyl radical,in the presence of a basic catalyst, in which(a) all of the ester III is placed in the reactor and is heated to the reaction temperature, and the amine II is metered in in the form of a melt while the reaction proceeds, while alcohol R.sup.3 --OH formed is continuously removed by distillation,(b) the reaction is carried out at a temperature of from 55.degree. to 110.degree. C., and(c) the reaction is carried out in the absence of organic solvents.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: July 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Beate Strecker, Helmut Wolf, Gerhard Wolf, Alfred Oftring, Hans-Heinrich Bechtolsheimer, Dieter Hertel
  • Patent number: 5534642
    Abstract: Chemical synthesis of amido acids, and their conversion to amido acid phenyl ester sulfates for use as bleach activators, starting from carboxylic acids and lactams.
    Type: Grant
    Filed: February 23, 1995
    Date of Patent: July 9, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Stephen W. Heinzman, Jeffrey S. Dupont, William C. Tettenhorst
  • Patent number: 5523431
    Abstract: The present application relates to a method of producing an amide product mixture having a low content of secondary amines by reacting an amide product mixture having a high secondary amine content with an aliphatic alkylene oxide in the absence of an essential amount of any alkoxylation catalyst. The amide product mixture obtained contains a minor amount of tertiary amines and exhibits advantageous properties when used for the formulation of cosmetic products, such as shampoos and creams; foam cleaning compositions, e.g. for textiles and cars; and functional fluids, such as lubricants, metal working fluids and hydraulic fluids.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: June 4, 1996
    Assignees: Berol Nobel AB, Castrol Ltd.
    Inventor: Rolf Skold
  • Patent number: 5508454
    Abstract: The present invention relates to novel quaternary ammonium derivatives wh have properties similar to those of non-ionic, amphoteric and cationic surfactants, to their preparation and to their use as surfactants in foaming and emulsifying compositions intended for use in the fields of pharmaceutics, cosmetics, hygiene and detergency.These derivatives have the general formula ##STR1## wherein essentially R is an alkyl or alkenyl radical having from 5 to 29 carbon atoms, R.sub.1 and R.sub.2 are an alkyl radical having from 1 to 4 carbon atoms, R.sub.3 is a 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, methyl or 2,3,4,5,6-pentahydroxyhexyl radical and X is a halogen atom or a hydroxyl group.
    Type: Grant
    Filed: August 4, 1994
    Date of Patent: April 16, 1996
    Assignee: Societe d'Exploitation de Produits pour les Industries Chimiques -SEPPIC
    Inventors: Bernard Brancq, Jean-Pierre Boiteux
  • Patent number: 5504228
    Abstract: The invention relates to new acylamino acids obtained by acylation of hydrolysates of proteins containing, essentially, fibroin and sericin as, for instance, silk.The invention provides also various compositions containing the said acylamino acids, for use in the cosmetic, hygienic, therapeutic and agricultural fields.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: April 2, 1996
    Assignee: Laboratoires Phytocos
    Inventors: Jean Morelle, Eliane Lauzanne, Jacqueline Rothfuss
  • Patent number: 5498786
    Abstract: This invention relates to novel processes for synthesizing intermediates in the preparation of N-aryl and N-heteroarylamide inhibitors of the enzyme acyl coenzyme A: cholesterol acyltransferase (ACAT), and to novel intermediates used in such processes.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: March 12, 1996
    Assignee: Pfizer Inc.
    Inventors: Sarah E. Kelly, George Chang
  • Patent number: 5496959
    Abstract: This invention relates to the preparation of N-acyl taurates by the direct condensation of carboxylic acids with taurate (substituted 2-aminoalkane sulfonic acids and their alkali metal salts) derivatives.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: March 5, 1996
    Assignee: Hoechst Celanese Corporation
    Inventor: James F. Day
  • Patent number: 5470992
    Abstract: A method for the synthesis of betaines of the general formula ##STR1## by quaternizing the fatty acid amide dialkylamines of the general formula ##STR2## with .omega.-halogenalkylcarboxylic acids of the formula X-(CH.sub.2).sub.y COOH, wherein X is a halogen group, or their salts in aqueous solution, the reaction being carried out within a temperature range of 115.degree. to 180.degree. C., until organically bound chlorine can no longer be detected, the fatty acid amide dialkylamine optionally being quaternized partially or completely in a first step at 80.degree. to 100.degree. C.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: November 28, 1995
    Assignee: Th. Goldschmidt AG
    Inventors: Burghard Gruning, Willi Foitzik, Christian Weitemeyer, Hans-Dieter Kaseborn
  • Patent number: 5434276
    Abstract: A process for the preparation of an N-acyl tauride comprising reacting an aliphatic or alicyclic carboxylic acid having from 6 to 22 carbon atoms with a taurine salt having the formula:HNR.sub.1 --CHR.sub.2 --CHR.sub.3 --SO.sub.3 Mwherein R.sub.1 is H or a C.sub.1 to C.sub.20 hydrocarbon radical; R.sub.2 and R.sub.3 are each independently H, or C.sub.1 -C.sub.6 hydrocarbon radical; M is a salt forming radical selected from the group consisting of alkali metals and alkaline earth metals; in a substantially inert atmosphere in the presence of an alkali metal borohydride, wherein the alkali metal is selected from the group of sodium, potassium, lithium and ammonium to produce a reaction product containing N-acyl tauride.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: July 18, 1995
    Assignee: Finetex, Inc.
    Inventors: Ismail I. Walele, Samad A. Syed
  • Patent number: 5414099
    Abstract: Chemical synthesis of amido acids, and their conversion to amido acid phenyl ester sulfates for use as bleach activators, starting from carboxylic acids and lactams.
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: May 9, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Stephen W. Heinzman, Jeffrey S. Dupont, William C. Tettenhorst
  • Patent number: 5393901
    Abstract: This invention relates to a process for preparing amido-carboxylic acids in water wherein hydrolysis and amidation reactions are conducted simultaneously in a single vessel. The process involves three steps. The first step involves heating at a temperature of 150.degree. C.-300.degree. C. for 2 to 10 hours, a mixture containing water, a nitrogen containing compound selected from the group consisting of a lactam and an amino acid, and a carboxylic acid or ester. The second step involves cooling the reaction mixture to obtain a two phase system containing an aqueous layer and an organic layer. The third step involves separating the amido-carboxylic acid containing organic layer from the aqueous layer. The presence of water aids in product isolation by phase separation and recycle of the reactants.Amido-carboxylic acids are used to make bleach activators for detergents.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: February 28, 1995
    Assignee: Eastman Chemical Company
    Inventors: George C. Zima, T. Hugh Williams, Gary P. Lutz, William C. Dickason
  • Patent number: 5393902
    Abstract: A process is reported for the preparation of bis(amidocarboxylic acid) involving reacting an ester with an aminocarboxylate compound, the latter being formed from lactams or aminocarboxylic acids and salts thereof. The ester and aminocarboxylate compound are present in a weight ratio of about 1:1 to about 1:4, and reaction is conducted in a mono- or polyhydric alcohol solvent.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: February 28, 1995
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Janet L. Coope, AnneMarie Brescia, Michael I. Hill, Martina Santoso, Stephen A. Madison
  • Patent number: 5391780
    Abstract: This invention relates to a process for preparing amido-carboxylic acids in water. The process involves four steps. Step (A) involves hydrolyzing a lactam at a temperature of 150.degree. C.-300.degree. C. to form a mixture containing an amino acid. Step (B) involves cooling the reaction mixture formed in Step (A) to a temperature of 25.degree. C.-100.degree. C. Step (C) involves reacting a carboxylic acid anhydride with the amino acid formed in Step (A) to form a reaction mixture containing an organic layer which contains an amido-carboxylic acid and an aqueous layer. Step (D) involves separating the amido-carboxylic acid containing organic layer from the aqueous layer. The presence of water aids in product isolation by phase separation and recycle of the reactants. Amido-carboxylic acids are used to make bleach activators for detergents.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: February 21, 1995
    Assignee: Eastman Chemical Company
    Inventors: George C. Zima, T. Hugh Williams
  • Patent number: 5380891
    Abstract: Disclosed is a process for manufacturing a linear glucamide surfactant comprising reacting an N-alkylglucamine, e.g., N-methylglucamine, a fatty ester, e.g., coconut oil in the presence of a phase transfer agent, generally a nonionic surfactant, preferably a preformed product of the process, the reaction preferably being conducted in the presence of an alkaline catalyst.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: January 10, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Daniel S. Connor, Jeffrey J. Scheibel, Ju-Nan Kao
  • 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: 5371250
    Abstract: The process described relates to the preparation of aqueous betaine solutions by reaction of a tertiary amine with an .omega.-monohalocarboxylic acid, preferably monochloroacetic acid, and an alkali metal hydroxide in the presence of water, which solutions are said to be highly pure particularly in respect of the tertiary starting amine and .omega.-monohalocarboxylic acid. This is achieved by first reacting the three reaction components in a certain molar ratio with the aim of obtaining a betaine solution which comprises only a tolerated amount of starting amine. This aqueous betaine solution is then treated with a sulfonating agent, preferably with an alkali metal sulfite, alkali metal pyrosulfite or alkali metal bisulfite, for conversion of the .omega.-monohalocarboxylic acid present into the corresponding sulfocarboxylic acid, which is not troublesome. The process described is simple to carry out and leads to the highly pure aqueous betaine solutions mentioned.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: December 6, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Seitz, Reinhard Vybiral
  • Patent number: 5354906
    Abstract: An aqueous liquid solution of a betaine of the following general formula is disclosed ##STR1## in which R is an alkyl group of coconut fatty acids, preferably hydrogenated coconut fatty acids, or a fatty acid mixture which, on the average, corresponds to coconut fatty acids, wherein the solution has a solids content of at least 40% by weight, a pH of 5 to 8 and an aminoamide content of not more than 1% by weight, characterized by a content of 1 to 3% by weight, based on the solution, of one or more saturated fatty acids with, on the average, 8 to 18 carbon atoms or one or more unsaturated fatty acids with, on the average, 8 to 24 carbon atoms and 0 to 4% by weight of glycerin, based on the solution.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: October 11, 1994
    Assignee: Th. Goldschmidt AG
    Inventors: Christian Weitemeyer, Willi Foitzik, Hans-Dieter Kaseborn, Burghard Gruning, Uwe Begoihn
  • Patent number: 5348995
    Abstract: A novel amine-free antistatic agent comprising the reaction product of diethanolamine and a fatty acid or fatty acid ester, neutralized with a strong acid is disclosed, along with plastic composition treated with said antistatic composition, as well as a method for making the antistatic composition and methods for using it to produce plastic articles with antistatic properties.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: September 20, 1994
    Assignee: PPG Industries, Inc.
    Inventor: Barbara J. Anderson
  • Patent number: 5318727
    Abstract: A cationic compound is useful for a cleaning agent such as shampooing and defined by the formula (I): ##STR1## in which R1 is straight or branched and an alkyl having 7 to 15 carbon atoms or an alkenyl having 7 to 15 carbon atoms; R2, R3 and R4, independently of one another, are an alkyl having 1 to 3 carbon atoms; G is hydrogen atom, an alkyl having 1 to 3 carbon atoms or a hydroxyalkyl having 1 to 3 carbon atoms, E is hydrogen atom, an alkyl having 1 to 3 carbon atoms, a hydroxyalkyl having 1 to 3 carbon atoms or an ammonium group having the formula (II): ##STR2## Y being hydrogen atom or hydroxy, A being hydroxy, a halogen atom or an alkylsulfate having 1 to 4 carbon atoms, m being 2 or 3, n being zero or an integer of 1 to 5, provided that (1) when G is an alkyl or a hydroxyalkyl, E is neither an alkyl nor a hydroxyalkyl, (2) when n is 1, Y is hydrogen atom or hydroxy and when n is zero, 2, 3, 4 or 5, Y is hydrogen atom and (3) G and E cannot both be hydrogen.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: June 7, 1994
    Assignee: Kao Corporation
    Inventors: Yasuki Ohtawa, Makoto Kubo, Hiroyuki Imoto, Takashi Matsuo, Kazuyuki Yahagi, Koshiro Sotoya
  • Patent number: 5312933
    Abstract: The present invention relates to a process of producing symmetrically structured difatty acid diamines by reacting mixtures of fatty acids or their esters with diamines, isolating the symmetrical difatty acid diamides from the reaction mixture by making use of their different solubilities and concentrating them by recrystallisation if necessary. The invention also provides for a process of isolating a fatty acid from a mixture of fatty acids wherein the difatty acid diamides produced in the process of the invention are saponified to yield the corresponding free fatty acid.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: May 17, 1994
    Assignee: Battelle-Institut e.V.
    Inventors: Rainer Frische, Jurgen Volkheimer, Klaus Wollmann, Herrmann Schomann, Judith Schneider, Alexander Ach, Renate Gross-Lannert, Bernd Best
  • Patent number: 5310959
    Abstract: Processes for preparing 5,8,11-eicosatriynoic acid as well as esters and amides thereof involves initially preparing the acid by reacting 1-decyne with 1,4-dihalo-2-butyne in the presence of a strong base to form 1-halo-2,5-tetradecadiyne which is then reacted with 5-hexynoic acid so as to form 5,8,11-eicosatriynoic acid. This acid can then be converted to the acid chloride form and reacted with an alcohol to form an ester or converted to a potassium salt and reacted with a halide also to form an ester, or after conversion to an acid chloride reacted with an amine in the presence of a tertiary amine to form an amide, or the acid can be reacted with carbonyldiimidazole in the presence of a solvent and excess amine to form an amide.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: May 10, 1994
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Serge Restle, Michel Colin
  • Patent number: 5298636
    Abstract: Polyhydroxy amines reacted with fatty acid esters yield polyhydroxy fatty acid amide surfactants, such as the C.sub.11 -C.sub.17 fatty N-methyl glucamides, which may be contaminated with secondary amines. Such amines are acylated by a reaction with acetic anhydride. The resulting "clean" polyhydroxy fatty acid amide surfactants are preferred for use in the presence of oxidants, especially in the formulation of modern, colorless liquid detergents.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: March 29, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Daniel S. Connor, Mark Hsiang-Kuen Mao
  • Patent number: 5239095
    Abstract: A method is disclosed for the preparation of flowable, aqueous dispersions, which contain 10 to 30% by weight of betaines of the general formula ##STR1## wherein R.sup.1 is a linear alkyl group with at least 16 carbon atoms or the R.sup.4 CONH(CH.sub.2).sub.x -- group, in which R.sup.4 CO is an acyl group derived from a saturated, linear fatty acid with at least 16 carbon atoms and x=2 or 3,R.sup.2, R.sup.3 are the same or different and in each case represent an alkyl group with 1 to 4 carbon atoms,y is 1, 2 or 3,by quaternizing a tertiary amine of the general formulaR.sup.1 --NR.sup.2 R.sup.3with .omega.-halogenalkylcarboxylic acids X(CH.sub.2).sub.y COOY or their salts (X=halogen group, Y=hydrogen, alkali or ammonium) in an aqueous or alcoholic, aqueous solution at elevated temperature. Anionic surfactants are added to the reaction mixture before the quaternization reaction in such amounts, that the ultimate dispersion contains 1 to 10% by weight of anionic surfactants.
    Type: Grant
    Filed: October 31, 1991
    Date of Patent: August 24, 1993
    Assignee: Th. Goldschmidt AG
    Inventor: Volkbert Bade
  • Patent number: 5210227
    Abstract: Compounds of formula I, ##STR1## wherein R.sup.1 represents H, OH, protected OH or alkoxy; R.sup.2 represents H; R.sup.3 represents O or (H,OH); R.sup.4 represents methyl, ethyl, propyl or allyl; R.sup.5 represents OH, protected OH or alkoxy; R.sup.6 represents OH; R.sup.7 represents OH, alkoxy or NR.sup.8 R.sup.9 where R.sup.8 and R.sup.9 independently represent H, alkyl or aryl; in addition, R.sup.1 and R.sup.2 may together represent a second bond between the carbon atoms to which they are attached; and R.sup.6 and R.sup.7 may together represent O; and pharmaceutically acceptable salts thereof; are useful inter alia as immunosuppressive agents. The invention also provides the novel compounds of formula I.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: May 11, 1993
    Assignees: Fisons plc, Fujisawa Pharmaceutical Company Limited
    Inventors: Hirokazu Tanaka, Martin E. Cooper, David K. Donald
  • Patent number: 5210207
    Abstract: The invention provides an improved process for the preparation of a vinyl derivative of a Bronsted acid, wherein a vinyl derivative of a first Bronsted acid is subjected to transvinylation by reactive distillation with a second Bronsted acid.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Morteza Mokhtarzadeh, Rex E. Murray
  • Patent number: 5208355
    Abstract: Novel amide derivatives have the following structure (1): ##STR1## where Y is hydrogen or an unsaturated fatty acid residue,A is an hydroxyalkyl group,B is a sugar or phosphate residue, and(C.sub.a H.sub.b) is a hydrocarbon residue with from 7 to 49 carbon atoms.The amide derivative can be employed in compositions, together with a suitable carrier, for topical application, particularly to improve damaged human skin or hair.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: May 4, 1993
    Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.
    Inventor: Ian R. Scott
  • Patent number: 5110508
    Abstract: The invention relates to a process, more especially a discontinuous process, for conducting a reaction taking place at elevated temperature in which heat-sensitive products are formed. To increase the volume-time yield, a heat transfer unit independent of the reactor is used for heating. The invention also relates to an apparatus for the production of heat-sensitive products at elevated temperatures. This apparatus comprises a reactor and a heating system. To increase the volume-time yield, the heating system comprises at least one heat transfer unit arranged outside and connected to the reactor.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: May 5, 1992
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Karl-Heinz Buettgen, Bernhard Gutsche, Friedrich Hommers, Wilhelm Johannisbauer, Eberhard Peukert, Reinhold Sedelies
  • Patent number: 5103055
    Abstract: Disclosed is a method which comprises the reaction in a reaction zone of a nitrile, RCN, with a hydroxyl compound, R'OH, in the presence of water introduced into the reaction zone in the amount of more than 0.15 mole and up to 10 moles, per mole of RCN introduced to the reaction zone, thereby producing a reaction mixture containing at least one amide selected from R--CONHR' and R--CON(R').sub.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: April 7, 1992
    Assignee: The Standard Oil Company
    Inventor: Mark C. Cesa