Amidation Patents (Class 554/69)
  • Patent number: 6828452
    Abstract: Acylamino acids are made by a process which comprises the steps of: (1) introducing a mixture comprised of at least one amino acid or amino acid salt and an alkali source into a reaction zone; (2) adding a mixture comprised of a fatty acid halide of the formula (I): R1COX  (I) wherein R1 is an alkyl or alkenyl group having from 6 to 22 carbon atoms and X is chlorine, bromine or iodine to form a reaction mixture while continuously circulating the reaction mixture from the reaction zone through a mixing zone until all of the second mixture has been added to the reaction zone. The process guarantees uniform mixing of the reaction components without the foaming observed without the use of a mixing zone.
    Type: Grant
    Filed: July 15, 2003
    Date of Patent: December 7, 2004
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Hans-Christian Raths, Andreas Syldath, Karl Heinz Schmid, Juergen Falkowski, Ingomar Mrozek, Josef Koester
  • Publication number: 20040063980
    Abstract: Acylamino acids are made by a process which comprises the steps of: (1) introducing a mixture comprised of at least one amino acid or amino acid salt and an alkali source into a reaction zone; (2) adding a mixture comprised of a fatty acid halide of the formula (I):
    Type: Application
    Filed: July 15, 2003
    Publication date: April 1, 2004
    Inventors: Hans-Christian Raths, Andreas Syldath, Karl Heinz Schmid, Juergen Falkowski, Ingomar Mrozek, Josef Koester
  • Patent number: 6703517
    Abstract: A method for preparing a highly purified N-long chain acyl neutral amino acid for use of a detergent and the like in a simple and convenient manner and in a high yield by reacting a neutral amino acid such as glycine, &ggr;-aminobutyric acid, and alanine, with a saturated or unsaturated fatty acid halide having 8 to 22 carbon atoms, wherein the reaction is performed in a mixture of water and one or more kinds of hydrophilic organic solvents selected from the group consisting of acetone, acetonitrile, a secondary alcohol having 3 or 4 carbon atoms, and a tertiary alcohol having 4 carbon atoms such as isopropanol, sec-butanol, and tert-butanol in the presence of a base.
    Type: Grant
    Filed: November 22, 2002
    Date of Patent: March 9, 2004
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tatsuya Hattori, Nobuyoshi Kitamura, Naoya Yamato, Hirofumi Yokota
  • Patent number: 6562874
    Abstract: Composition may be prepared in a single DEFI reactor comprising mixtures of (1) DEFI (directly esterified fatty acyl isethionate) and (2) a compound produced by the reaction of (a) isethionate with a fatty acid replacement (e.g., a multicarboxylic fatty acid, a fatty acid); or (b) fatty acid with an isethionate replacement (e.g., C2-C24 alcohols, C2-C20 organic acids, amines). Such mixtures are milder than DEFI alone while retaining substantially same foaming benefit.
    Type: Grant
    Filed: December 7, 1999
    Date of Patent: May 13, 2003
    Assignee: Unilever Home & Personal Care USA division of Conopco, Inc.
    Inventors: Leonora Ilardi, Lee Ann Gallagher, Michael Massaro
  • Patent number: 6515153
    Abstract: The present invention relates to the formation of an amido ester having the formula: R1—CO—NR3—R2—COL or R1—NR3—CO—R2—COL wherein R1 is C1-C12 linear or branched alkyl, C6-C14 aryl, C7-C14 alkyl substituted aryl unit; R2 is C1-C14 alkylene, C6-C14 arylene, C7-C14 alkyl substituted arylene; R3 is hydrogen, C1-C10 alkyl, C6-C10 aryl, C7-C10 alkyl substituted aryl, L is a aryl leaving group having the formula: R4 comprises one or more anionic or cationic units, wherein said compound is formed using a spinning disc reactor.
    Type: Grant
    Filed: August 30, 2001
    Date of Patent: February 4, 2003
    Assignee: The Procter & Gamble Company
    Inventors: Michael Eugene Burns, Michael Steven Gibson, David William York
  • Patent number: 6497888
    Abstract: A process, composition, and kit for limiting the penetration into the skin and/or the keratinous fibers of at least one cosmetically and/or pharmaceutically active agent present in a base cosmetic and/or pharmaceutical composition for topical application and in particular for reducing the rate of penetration into the skin and/or the keratinous fibers of the active agent(s).
    Type: Grant
    Filed: October 13, 2000
    Date of Patent: December 24, 2002
    Assignee: L'Oréal S.A.
    Inventors: Jean-Luc Morancais, Michel Philippe
  • Patent number: 6444832
    Abstract: Compounds of formula I in which R1 denotes hydrogen or methyl R2 denotes lower straight-chained or branched alkyl with 1 to 10 carbon atoms R3 denotes hydrogen or lower alkyl n denotes 0-12 R4 denotes alkyl, alkenyl or alkinyl with 6 to 24 carbon atoms, processes for the production thereof as well as pharmaceutical agents containing these compounds for the treatment of osteoporosis.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: September 3, 2002
    Inventors: Angelika Esswein, Lothar Kling, Ulrike Leser, Walter-Gunar Friebe
  • Patent number: 6369249
    Abstract: The present invention relates to a process for the preparation of N-substituted acrylamides of the general formula CH2═CH—CONHR, wherein, R is alkyl group having carbon 1 to 22 or acyl group having carbon 1 to 18. The process for the preparation of the N-substituted acrylamides comprises reacting acrylamide with alkyl acyl chloride in the presence of Lewis acid catalyst in an organic solvent at a temperature ranging between room temperature to 50° C. for a period ranging between 1 hour to 24 hours.
    Type: Grant
    Filed: February 2, 2000
    Date of Patent: April 9, 2002
    Assignee: Council of Scientific & Industrial Research
    Inventors: Bhalchandra Shripad Lele, Mohan Gopalkrishna Kulkarni
  • Publication number: 20020035281
    Abstract: The present inventintion relates to the formation of an amido ester having the formula:
    Type: Application
    Filed: August 30, 2001
    Publication date: March 21, 2002
    Applicant: The Procter & Gamble Company
    Inventors: Michael Eugene Burns, Michael Steven Gibson, David William York
  • Patent number: 6350889
    Abstract: A compound of formula (1), and compositions containing a plurality of such compounds, wherein, independently at each occurrence, R1 is a linear alkyl group having at least twenty carbons; R2 is selected from the diradical that results when two carboxyl groups are removed from polymerized fatty acid, and a linear C4-12 hydrocarbon group, with the proviso that at least one occurrence of R2 is the diradical that results when two carboxyl groups are removed from polymerized fatty acid; R3 is a diradical selected from C2-36 hydrocarbons and C4-30 poly(alkyleneoxides); X is selected from O and NH such that X—R3—X is selected from O—R3—O and NH—R3—O; and n represents a number of repeating units selected from 1-5, may be used as a vehicle for hot melt printing inks, including inks for ink jet printing.
    Type: Grant
    Filed: June 24, 1999
    Date of Patent: February 26, 2002
    Assignee: Arizona Chemical Company
    Inventor: Mark S. Pavlin
  • Patent number: 6335370
    Abstract: Aqueous-alcoholic solutions of coconut or palm oil alkylamidopropylbetaines with a betaine content of greater than 50%, which are fluid, stable and pumpable are described as occupying a well-defined zone of their betaine/water/ethanol ternary diagram. They are prepared by synthesis and quaternization of the amidoamine directly in the solvent medium in which they are defined.
    Type: Grant
    Filed: February 2, 2000
    Date of Patent: January 1, 2002
    Assignee: Ceca S.A.
    Inventors: Regine De Mesanstourne, Stephane Fouquay, Jean-Paul Gamet, Francois Guillemet
  • Patent number: 6316644
    Abstract: The present invention relates to a polyethoxylated retinamide derivative represented by formula (I), which is useful as an agent for inhibiting skin aging; in R represents hydrogen or C1-6 lower alkyl and n denotes the number of 2 to 100, and the process for preparing the compound of formula (I) as an effective component.
    Type: Grant
    Filed: September 27, 2000
    Date of Patent: November 13, 2001
    Assignee: LG Chemical Ltd.
    Inventors: Bong Youl Chung, Young Keun Kim, In Sang Lee, Bong Jun Park, Wan Goo Cho, Young Sook Song, Mun Eok Park, Young Deuk Kim, Sung Jun Lee
  • Patent number: 6294681
    Abstract: The present invention provides a process for producing N-acyl-protected amino acids with the general formula I by amidocarbonylation whereby carbon monoxide, an amide/nitrile and an aldehyde, are reacted in the presence of a metal catalysts such as rhodium, iridium or ruthenium catalysts.
    Type: Grant
    Filed: June 26, 2000
    Date of Patent: September 25, 2001
    Assignee: Degussa-Huels AG
    Inventors: Karlheinz Drauz, Olaf Burkhardt, Matthias Beller, Markus Eckert, Wahed Moradi, Helfried Neumann
  • Patent number: 6274748
    Abstract: The invention relates to a process for making compounds having fatty acid moieties by reacting a fatty acid with a (hydroxyalkyl)amino alkane acid or a (hydroxyalkyl)amine and an aqueous base followed by heating the reaction mixture. The process is particularly useful for the formation of di-fatty acid esters from BES, and tri-fatty acid esters from TES. The reaction parameters can be adjusted to produce useful additional products of the TES-trioleate, including fatty acid amides of mono-, di- and tri-oleoyl-TES.
    Type: Grant
    Filed: April 14, 2000
    Date of Patent: August 14, 2001
    Assignee: Zenith Cosmetic Technologies LLC
    Inventor: John M. Young
  • Publication number: 20010007038
    Abstract: The invention is a catalyst, the use of the catalyst and a method of using the catalyst in the formation of a compound with an amide bond.
    Type: Application
    Filed: February 22, 2001
    Publication date: July 5, 2001
    Inventor: William Leonard Scott
  • Patent number: 6239298
    Abstract: There is disclosed a fuel lubricity additive, made by a two-step process wherein the first step is co-reacting an unsaturated base oil, predominantly from vegetable oil sources, and a compound having a diene structure and a carboxylic acid group, wherein the second step is esterifying or amidifying the free carboxylic acid group of anhydride group with a poly-hydroxy-containing compound or poly-amine compound to form the final fuel lubricity additive useful in diesel fuels. The inventive fuel lubricity additive also is useful as a dispersant.
    Type: Grant
    Filed: May 26, 1998
    Date of Patent: May 29, 2001
    Assignee: International Lubricants Inc.
    Inventors: Will F. Williamson, Phillip S. Landis, Blaine N. Rhodes
  • Patent number: 6207843
    Abstract: N-(alkanoyl)aminoalkanoyloxybenzensulfonate bleach activators are prepared in an improved process using amine catalyst and/or amido solvents.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: March 27, 2001
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey Scott DuPont, Stephen Wayne Heinzman
  • Patent number: 6121470
    Abstract: Glycine derivatives represented by the following formula (1) and cleanser compositions containing the same: ##STR1## wherein R is a linear or branched alkyl group having 11 to 13 carbon atoms, a linear or branched alkenyl group having 11 to 13 carbon atoms, or a linear or branched hydroxyalkyl group having 11 to 13 carbon atoms, and M.sub.1 and M.sub.2 are the same or different from each other and each independently is a hydrogen atom, an alkali metal atom, 1/2 (an alkaline earth metal atom), an ammonium group, a monoalkanolammonium group having 1 to 22 carbon atoms, a dialkanolammonium group having 2 to 22 carbon atoms in total, a trialkanolammonium group having 3 to 22 carbon atoms in total, or a protonated basic amino acid, are excellent in foaming, detergency, comfort in use and safety, are antipollutive and can be used for various purposes, for example, a cleanser composition for the hair and body or tableware.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: September 19, 2000
    Assignee: Kao Corporation
    Inventors: Masakatsu Takahashi, Hiromoto Mizushima, Hiroe Tanahashi, Toshio Nozaki
  • Patent number: 6121471
    Abstract: The invention is a catalyst, the use of the catalyst and a method of using the catalyst in the formation of a compound with an amide bond. The catalyst is an HOBT derivative having the following formula (1): ##STR1## where R.sup.1 is a group bearing a positive charge at pH 5-7; where Y is a bond or a substituted or unsubstituted alkylene chain containing 1-10 carbon atoms and 0-2 heteroatoms selected from the group consisting of N, S and O; and where X is a linker group selected from --CO-- or --SO.sub.2 --. In the method, an amine, a carboxylic acid, an amide coupling agent and a catalyst of formula (1) are reacted for a time sufficient to produce an amide bond between the amine and the carboxylic acid. Thereafter, the compound containing the amide bond is isolated.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: September 19, 2000
    Assignee: Eli Lilly and Company
    Inventor: William Leonard Scott
  • Patent number: 6107498
    Abstract: Methods for producing carboxylic amides involves combining near-stoichiometric amounts of carboxylic acid and amine in a reaction vessel and reacting under pressures greater than atmospheric pressure. Alternatively, an excess of amine is reacted with carboxylic acid at atmospheric pressure to produce a carboxylic amide.
    Type: Grant
    Filed: April 22, 1997
    Date of Patent: August 22, 2000
    Assignee: AKZO Nobel N.V.
    Inventors: Bernard Maisonneuve, Dale Steichen, Ralph Franklin, Kornelis Overkempe
  • Patent number: 6093839
    Abstract: Process for the preparation of acylglutamate solutions by reaction of a glutamic acid salt with an acid chloride in water and in the presence of an anionic or zwitterionic surfactant.
    Type: Grant
    Filed: February 17, 1999
    Date of Patent: July 25, 2000
    Assignee: Clariant GmbH
    Inventors: Thomas Hingott, Joachim Hess
  • Patent number: 6069261
    Abstract: A process carried out in a reaction column for the chemical reaction of substances the reaction of which is affected by an unfavorable equilibrium position of the main reaction or a preceding equilibrium, wherein during the reaction one or more substances to be separated are continuously removed from the reaction mixture by one or more auxiliaries.
    Type: Grant
    Filed: May 4, 1998
    Date of Patent: May 30, 2000
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Ulrich Hoffmann, Ulrich Kunz
  • Patent number: 6060612
    Abstract: Disclosed herein is a ceramide-like compound having properties of the natural ceramides, and a method for producing the same, and a cosmetic composition containing the same as a active ingredient.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: May 9, 2000
    Assignee: Pacific Corporation
    Inventors: Jong Eon Hong, Myeung Su Ku, Bo Sub Lee, Young Hun Byon, Duk Hee Kim, Sang Rhin Lee, Ok Sob Lee, Hae Kwang Lee, Jong Ho Park, Ki Wha Lee, Ki Tack Nam, Jong Il Kim, Hyun Jun Kim, Hey Jin Jung
  • Patent number: 6060613
    Abstract: Provided is an industrially advantageous process for producing an N-long chain acyl acidic amino acid by condensing an acidic amino acid with a long chain fatty acid halide in water in the presence of an alkali, wherein the reaction is performed in the presence of a polyhydric alcohol. The desired product is obtained in a high yield without the problems of odor and of safety owing to organic solvents and catalyst remaining in the desired product. The equipment for removal of the solvents is reduced, and production is simplified.
    Type: Grant
    Filed: February 5, 1998
    Date of Patent: May 9, 2000
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tatsuya Hattori, Kiyomiki Hirai
  • Patent number: 6057464
    Abstract: The invention relates to high-foaming zwitterionic and anionic surfactants which are prepared by sulfation of N,N-dialkylaminoalkyl-sugar amides, preferably using gaseous sulfur trioxide. The invention furthermore relates to compositions which comprise known surfactants and suitable solvents, in addition to the novel active compounds. The novel surfactants are particularly suitable for detergents and cosmetic formulations.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: May 2, 2000
    Assignee: Clariant GmbH
    Inventor: Bernd Papenfuhs
  • Patent number: 6054483
    Abstract: The invention relates to fatty acids conjugated to amino acids and their derivatives that elicit the production and/or release of plant volatiles compounds which attract and/or retain beneficial insects and deter herbivorous insect feeding. These conjugates also induce plants to increase production of pharmacologically important compounds such as taxol, increase fragrance of flowers, and increase production of plant essential oil. The invention also relates to methods for isolating the compounds from herbivorous insect oral secretions and to chemically synthesizing the compounds and their active derivatives.
    Type: Grant
    Filed: December 3, 1996
    Date of Patent: April 25, 2000
    Assignees: The United States of America as represented by the Secretary of Agriculture, Virginia Military Institute Research Laboratories, Inc.
    Inventors: James H. Tumlinson, III, Hans T. Alborn, John H. Loughrin, Theodoor C. J. Turlings, Tappey H. Jones
  • Patent number: 6054599
    Abstract: Novel phytosphingosine-based analogs of ceramide I, methods for the preparation of these novel compounds, cosmetic and pharmaceutical compositions containing such compounds, and methods for the use thereof are described.
    Type: Grant
    Filed: May 5, 1998
    Date of Patent: April 25, 2000
    Assignee: DSM N.V.
    Inventors: Pieter Gijsbert Weber, Johannes Wilhelmus Jacobus Lambers, Hein Simon Koger, Jan Verweij
  • Patent number: 6034257
    Abstract: In a process for preparing an alkoxylated amide of the formula (I)R.sup.1 --CO--NR.sup.2 --CHR.sup.3 --CHR.sup.4 --O--(CHR.sup.5 --CHR.sup.6 --O).sub.n --H (I)(1) glycerides of the fatty acids, specified later on, of the formula (II):R.sup.1 --COOH (II)are reached with amines of the formula (III)HNR.sup.2 R.sup.7 (III)to give amides of the formula (IV)R.sup.1 --CO--NR.sup.2 --R.sup.7 (IV)and glycerol,(2) then the glycerol which has been formed is separated off by adding of aqueous acid solution to the reaction mixture until it has a pH in the range 1-7, in order to bring about phase separation into a glycerol-containing aqueous phase and an organic phase containing amides of the formula (IV), and separating off the aqueous phase, and(3) subsequently the amide of the formula (IV) is reacted with ethylene oxide and/or propylene oxide and/or butylene oxide to give alkoxylated amides of the formula (I).
    Type: Grant
    Filed: June 3, 1999
    Date of Patent: March 7, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Oftring, Gunter Oetter, Richard Baur, Oliver Borzyk, Bernd Burkhart, Christian Ott, Martin aus dem Kahmen
  • Patent number: 6008390
    Abstract: N-long-chain acyl acidic amino acids or salts thereof are prepared by condensing an acidic amino acid or a salt thereof and a C.sub.8 -C.sub.22 long-chain fatty acid chloride in an aqueous solvent with stirring at a stirring power of not less than 0.2 kW/m.sup.3 while keeping the pH in the range of 10-13.
    Type: Grant
    Filed: September 8, 1997
    Date of Patent: December 28, 1999
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tatsuya Hattori, Kiyomiki Hirai
  • Patent number: 5962708
    Abstract: The invention relates to a process for the preparation of highly concentrated free-flowing and pumpable aqueous solutions of betaines by quaternization of a compound which contains tertiary amine nitrogen with a .omega.-halo carboxylic acid characterized in that 0.5-5% by weight of the final product, of a viscosity-reducing compound such as an alkali or alkaline earth metal citric acid salt is added to the reaction mixture before or during the quaternization reaction.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: October 5, 1999
    Assignee: Witco Surfactants GmbH
    Inventors: Ingo Hamann, Hans-Jurgen Kohle, Winfried Wehner
  • Patent number: 5959127
    Abstract: The ceramides according to the invention are compounds corresponding to the formula: ##STR1## in which: R.sub.1 is a C.sub.11 to C.sub.21 alkyl or alkenyl radical; R.sub.2 is a linear or branched C.sub.1 to C.sub.29 hydroxyalkyl radical or a C.sub.7 to C.sub.29 hydroxyaralkyl radical, these compounds being in the form of a racemic mixture of the erythro and threo diastereoisomers for the aminodiol part ##STR2## in erythro:threo ratios of from 85:15 to 20:80. Application to cosmetic and dermopharmaceutical compositions.
    Type: Grant
    Filed: September 4, 1997
    Date of Patent: September 28, 1999
    Assignee: L'OREAL
    Inventors: Didier Semeria, Michel Philippe, Claude Mahieu
  • Patent number: 5942635
    Abstract: In a process and an apparatus for the continuous preparation of N-acylamino carboxylic acids and N-acylamino sulfonic acids, and their alkali metal salts, from the alkali metal salts of amino carboxylic acids and amino sulfonic acids, respectively, and carbonyl halides in a reactor designed as circulating circuit, the reactants are fed for immediate reaction into the circulating circuit, and a part of the product solution corresponding to the amount fed in is continuously discharged from the circulating circuit. The reactants are circulated by a circulating pump. The temperature in the reactors is controlled. The heat produced in the reaction is removed.
    Type: Grant
    Filed: April 30, 1998
    Date of Patent: August 24, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Beate Ehle, Georg Schuh, Martin aus dem Kahmen, Dieter Hertel
  • Patent number: 5925775
    Abstract: Amidopropyl-N-alkyl-polyhydroxyalkylamines of the following formula (1) ##STR1## in which Z is a linear polyhydroxyhydrocarbon radical having at least 2 free or oxyalkylated hydroxyl groups, R.sup.1 is a C.sub.1 to C.sub.7 -alkyl radical or C.sub.2 to C.sub.4 -hydroxyalkyl radical and COR is an aliphatic acyl radical having 6 to 22 carbon atoms, and salts thereof from an inorganic or organic acid are described. They are prepared by a) reaction of a compound of the formula (2) ##STR2## with acrylonitrile to give the compound of the formula (3) ##STR3## b) hydrogenation of the product obtained in step a) to give the compound of the formula (4) ##STR4## and c) monoacylation of the product obtained in step b) in the melt to give the compound of the formula (1) mentioned. The compounds according to the invention are readily soluble in water and water/alcohol mixtures and are advantageous co-surfactants for use in detergents and cleaning compositions and in cosmetic preparations for cleansing the hair and skin.
    Type: Grant
    Filed: August 2, 1996
    Date of Patent: July 20, 1999
    Assignee: Clariant GmbH
    Inventors: Gunter Prossel, Reinhard Vybiral, Werner Skrypzak, Hans Jurgen Scholz
  • Patent number: 5919960
    Abstract: The present invention describes phytospringosine-based analogs of ceramides I, as well as cosmetics and pharmaceutical compositions containing these novel compounds and their use.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: July 6, 1999
    Assignee: Gist-brocades, B.V.
    Inventors: Pieter Gijsbert Weber, Johannes Wilhelmus Jacobus Lambers, Hein Simon Koger, Jan Verweij
  • Patent number: 5766612
    Abstract: The use of endgroup-capped fatty amide alkoxylates IR.sup.1 --CO--NH--(CH.sub.2).sub.n --O--(AO).sub.x --R.sup.2(I)whereR.sup.1 is C.sub.5 -C.sub.21 -alkyl or -alkenyl,R.sup.2 is C.sub.1 -C.sub.4 -alkyl,A is C.sub.2 -C.sub.4 -alkylene,n is 2 or 3, andx has a value from 1 to 6,as nonionic surfactants or emulsifiers in detergents, cleaners or body care compositions, as surface-active substances for industrial applications in electroplating, in the photographic industry, in petroleum production, in the pharmaceutical industry, in plant feeding and in crop protection formulations, and as surface-active substances in the production of emulsions and pigment and plastic dispersions.
    Type: Grant
    Filed: April 22, 1996
    Date of Patent: June 16, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Beate Strecker, Gunter Oetter, Alfred Oftring, Johannes Perner, Richard Baur, Volker Schwendemann, Martin aus dem Kahmen, Wolfgang Reif
  • Patent number: 5750749
    Abstract: A process for preparing a surfactant composition comprising reacting an N-alkylpolyhydroxyamine and an alkoxylated triglyceride of a fatty acid to produce a mixture of a polyhydroxy-fatty amide, an alkoxylated monoglyceride of a fatty acid, and an alkoxylated diglyceride of a fatty acid, the resulting mixture providing a water soluble surfactant composition.
    Type: Grant
    Filed: February 9, 1996
    Date of Patent: May 12, 1998
    Assignee: CONDEA Vista Company
    Inventors: Upali Weerasooriya, John Lin
  • Patent number: 5728852
    Abstract: A method for producing a monoalkanol amide comprising the steps of (a) treating an entire amount of fatty acid with a monoalkanol amine in an amount of 0.7 to 0.95 times by mole of the amount of the fatty acid and more than 70% and not more than 90% by weight of the entire amount of the monoalkanol amine to yield a mixture mainly containing a monoalkanol amide and an amido monoester; and (b) treating the mixture obtained in step (a) with the remaining portion of the monoalkanol amine, wherein the molar ratio of the entire amount of the monoalkanol amine to that of the fatty acid is 1.0 to 1.3.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: March 17, 1998
    Assignee: KAO Corporation
    Inventors: Kenichi Nishikawa, Kazuhito Miyoshi, Yukiko Oshima, Hiroyuki Imoto
  • Patent number: 5723673
    Abstract: N-alkyl polyhydroxy alkyl amines such as N-methyl glucamine having a Gardner Color of less than 1 are reacted with sources of fatty acyl groups such as methyl esters, anhydrides, and/or fatty acids that have greater than 98% transmittance at 460 nm in organic hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amine amides with good color. The N-alkyl polyhydroxyamines can be purified by crystallization, and/or subjected to reductive bleaching, to provide superior color. The reaction is preferably carried out at low temperature for short periods of time and with low catalyst levels to minimize formation of cyclic products. The resulting amide product can be further purified by treatment with anionic and cationic exchange resins to remove soap and amine impurities. The anionic ion exchange resin can be readily regenerated by acidifying it followed by washing with an organic solvent.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 3, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Junan Kao, Ephraim Lamar Kelly, Vicki Lynn Weber, Michael Steven Gibson, Donald Benjamin Appleby, Joseph Fredrich Sherman, Ronald Edward Pegoli, Mary Celine Schneider, Terry Franklin Formyduval, Larry Nelson Hawkins
  • Patent number: 5717118
    Abstract: The present invention relates to a one-step process for preparing amido-carboxylic acid esters having the amide nitrogen positioned between two carbonyl carbons by reacting a carboxylic acid or carboxylic acid ester with a monohydric alcohol and either a lactam, amino-carboxylic acid or a polymeric amino-carboxylic acid. In this process, amidation, esterification, alcoholysis, and hydrolysis reactions occur simultaneously.
    Type: Grant
    Filed: September 5, 1995
    Date of Patent: February 10, 1998
    Assignee: Eastman Chemical Company
    Inventors: Gary Paul Lutz, George Chester Zima, Thomas Hugh Williams
  • Patent number: 5710295
    Abstract: A process of preparing alkali metal N-acyl amino acids, especially sodium N-acyl sarcosinates. The process of the invention eliminates the use of phosphorus trichloride or thionyl chloride and carboxylic acid chlorides. The process involves reacting the alkali metal N-acyl amino acid directly with a fatty acid at elevated temperatures with constant removal of water generated in the reaction.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: January 20, 1998
    Assignee: Hampshire Chemical Corp.
    Inventors: Richard P. Woodbury, Roger R. Gaudette, F. David Wood
  • Patent number: 5688978
    Abstract: New and improved thickeners for mixtures of one or more surface active agent include beta-hydroxyalkyl-terminally branched fatty acid amides. The new and improved thickeners achieve the same or better viscosity with lower amounts of mineral salts being required to be added. Concomitant benefits such as improved softening, lubricity, emulsifying and foam intensifying properties are also achieved. The thickeners and cleaner compositions containing them may also be prepared so that they do not contain nitrosamines, unlike prior art amide thickeners. A preferred thickener in accordance with the invention is 2-hydroxypropyl-isostearyl amide. A novel method for making the preferred thickener, so that it is substantially free of undesirable impurities is also provided.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: November 18, 1997
    Assignee: Witco Corporation
    Inventors: Ginette Lefebvre, Line Fiquet
  • Patent number: 5681972
    Abstract: The invention relates to a process for preparing highly concentrated, free-flowing and pumpable, aqueous solutions of betaines by quaternization of compounds containing tertiary amine nitrogen with omega-halocarboxylic acids by known processes, which is characterized in that a) 30-100 equivalent-%, based on the amount of omega-halocarboxylic acid used, of Mg(OH).sub.2 and/or Ca(OH).sub.2 and b) 0-70 equivalent-%, based on the amount of omega-halocarboxylic acid used, of one or more NaOH, KOH and NH.sub.4 OH are added to the reaction mixture before or during the quaternization reaction.
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: October 28, 1997
    Assignee: Witco Surfactants GmbH
    Inventors: Ingo Hamann, Hans-Jurgen Kohle, Winfried Wehner
  • Patent number: 5681971
    Abstract: Fatty N-alkyl amides are synthesized directly from glycerides (preferably triglycerides) and amines in the absence of a catalyst, and preferably without a solvent. The method provides for products suitable for use without further purification, preferably after separating the glycerol and amide products. The disclosed method is also useful for the synthesis of glycerol from glycerides and ammonia and/or primary amines.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: October 28, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey John Scheibel, Robert Edward Shumate
  • Patent number: 5650527
    Abstract: This invention relates to a process for preparing amido ester compounds. The process involves (I) forming a mixture in a reactor of a phenol derivative and an amido-carboxylic acid at a temperature which ensures at least partial solubility of the phenol derivative and the amido-carboxylic acid, and (II) adding a carboxylic anhydride incrementally to the mixture formed in Step (I) while distilling a by-product carboxylic acid from the reactor. The amido esters are useful as bleach activators.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: July 22, 1997
    Assignee: Eastman Chemical Company
    Inventors: Gary Paul Lutz, George Chester Zima, William Charles Dickason
  • Patent number: 5646318
    Abstract: A process is provided for producing a hydroxyalkylamide which comprises reacting alkyl ester and alkanolamine in the presence of a catalyst to provide a reaction mixture containing hydroxyalkylamide product and low boiling alcohol by-product, solidifying the hydroxyalkylamide product, neutralizing the catalyst and recovering the hydroxyalkylamide product.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: July 8, 1997
    Assignee: Akzo Nobel nv
    Inventors: Maurice Dery, Nils Brolund
  • Patent number: 5646319
    Abstract: Chemical synthesis of N-acyl-N-alkylcarboxylates through oxidation of substituted amides formed from carboxylic acid esters and an N-alkyl-N-alkanolamine.
    Type: Grant
    Filed: June 23, 1995
    Date of Patent: July 8, 1997
    Assignee: The Procter & Gamble Company
    Inventors: James Carey Letton, Larry Eugene Miller
  • Patent number: 5646317
    Abstract: To provide processes suitable for industrial production by which high-purity N-(long-chain acyl)amino acid and salt thereof can be prepared from inexpensive raw materials.An alkyl ester of a fatty acid (2) is reacted with an aminonitrile (3) in the presence of a basic catalyst to form an amidonitrile (1), the amidonitrile (1) is hydrolyzed into an N-(long-chain acyl)amino acid salt (4) in the presence of a basic substance, the pH of the resulting aqueous solution is adjusted to a pH from 1 to 5 with a mineral acid to form an N-(long-chain acyl)amino acid (5), and this amino acid is recovered. ##STR1## wherein R.sup.1 CO-- represents a fatty acid residue having 8 to 22 carbon atoms; R.sup.2 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R.sup.3 represents an alkylene group having 1 to 5 carbon atoms; R.sup.4 represents an alkyl group having 1 to 4 carbon atoms; and M represents a monovalent cation.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: July 8, 1997
    Assignee: Kao Corporation
    Inventors: Youhei Kaneko, Kohshiro Sotoya
  • Patent number: 5627056
    Abstract: An efficient method of producing phytosphingosine-containing ceramide one comprising: (a) obtaining a phytosphingosine base from tetraacetylphytosphingosine (TAPS) by a deacetylation reaction wherein the TAPS is produced by fermentation of cells of the F-60-10 mating type strain of Hansenula ciferrii using a fed-batch mode and a non-fermentable carbon source; and (b) coupling together the phytosphingosine base and a fatty acid/.omega.-hydroxy fatty acid component wherein the .omega.-hydroxy fatty acid component is prepared by a process which includes Kolbe synthesis.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: May 6, 1997
    Assignee: Elizabeth Arden Co., Division of Conopco, Inc.
    Inventors: John Casey, Peter S. Cheetham, Peter C. Harries, Della Hyliands, John T. Mitchell, Anthony V. Rawlings
  • Patent number: 5616745
    Abstract: New lipopolyamines of general formula (I), their salts, their preparation and their use. ##STR1## n=1 to 5 and m=2 to 6 R represents a radical ##STR2## (R.sub.1 and R.sub.2 : aliphatic radical containing 12 to 22 carbon atoms; R: hydrogen atom or alkyl radical optionally substituted with phenyl), or a radical ##STR3## (X=CH.sub.2, CO; R.sub.3 and R.sub.4 aliphatic radical containing 11 to 21 carbon atoms), their preparation and their use.The lipopolyamines of general formula (I) are especially useful as vectors for the transfection of eukaryotic cells.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 1, 1997
    Assignee: Centre National de la Recherche Scientifique
    Inventors: Jean-Paul Behr, Jean-Philippe Loeffler
  • Patent number: 5587498
    Abstract: A method for amidation of carboxylic acids using a supported transition metal catalyst. The amides prepared by this inventive method are available in high-yield and excellent purity, without catalytic residue.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: December 24, 1996
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: James A. Krogh, Anita R. Mokadam, B. Brian Smith