Hydroxyalkyl Substituent On The Amido Nitrogen Patents (Class 554/66)
  • Patent number: 5869711
    Abstract: The present invention relates to compounds corresponding to the formula: ##STR1## the compounds being in the form of mixtures of isomers at least on the amino alcohol part of the said formula (I). The invention also relates to a process for their preparation and their use, in particular for the treatment and care of the skin, the hair, the nails and the eyelashes in cosmetics or in dermatology.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: February 9, 1999
    Assignee: L'Oreal
    Inventors: Michel Philippe, Bernadette Luppi, Didier Semeria
  • Patent number: 5863945
    Abstract: This invention relates to amide derivatives represented by the following formula (1), amide derivative synthesis intermediates represented by the following formula (2), (3) or (4), and external skin care preparations, cosmetic hair care formulations and bath medicines containing the amide derivatives (1): ##STR1## wherein R.sup.1 and R.sup.1a are, for example, tetradecyl or hexadecyl, R.sup.2 is, for example, tridecyl or pentadecyl, R.sup.3 is, for example, ethylene or trimethylene, R.sup.3a is, for example, trimethylene, and R.sup.4, R.sup.4a and R.sup.4b are, for example, methoxy or ethoxy. When added to external skin care preparations, bath medicines and cosmetic hair care formulations, the amide derivatives (1) exhibit advantageous effects such as skin-roughness preventing/curing effects and hair touch-feeling improving effects.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: January 26, 1999
    Assignee: Kao Corporation
    Inventors: Koichi Murayama, Masahide Hoshino, Hiroshi Kusuoku, Minoru Nagai, Kiyoko Sugino
  • Patent number: 5760258
    Abstract: The amine oxides described correspond to the following formula (1) ##STR1## in which RCO is an aliphatic acyl radical having 6 to 22 carbon atoms, Z is a linear polyhydroxyhydrocarbon radical having at least 3 optionally oxyalkylated hydroxyl groups, m is an integer from 1 to 4, R.sup.1 is C.sub.1 to C.sub.4 -alkyl or C.sub.2 to C.sub.4 -hydroxyalkyl and R.sup.2 is C.sub.1 to C.sub.4 -alkyl or C.sub.2 to C.sub.4 -hydroxyalkyl. The amine oxides and the aqueous, alcoholic or aqueous-alcoholic solutions are prepared by oxidation of corresponding tertiary amine compounds with hydrogen peroxide. The novel amine oxides and their solutions are particularly suitable for the preparation of surface-active compositions for hair and body care.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: June 2, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Bernd Papenfuhs
  • Patent number: 5753707
    Abstract: An amide derivative represented by the following formula (1): ##STR1## wherein R.sup.1 represents a C.sub.1-40 hydrocarbon; R.sup.2 represents a C.sub.1-6 alkylene; R.sup.3 represents H, OH or alkoxyl; R.sup.4 represents a C.sub.1-39 hydrocarbon; R.sup.5 represents ##STR2## with the proviso that when R.sup.5 represents ##STR3## R.sup.3 does not represent OH; and a composition of the amide derivative for topical application to human skin. The composition improves the barrier function of the stratum corneum, providing improvement and prevention of dermatitis, skin roughness, or similar disorders.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: May 19, 1998
    Assignee: Kao Corporation
    Inventors: Masahide Hoshino, Hiroshi Kusuoku, Tadashi Hase, Atsuko Otsuka, Ichiro Tokimitsu, Akira Yamamuro, Yoshiya Sugai, Koji Yoshino, Youichi Arai, Shinichi Meguro
  • Patent number: 5750748
    Abstract: A process for the preparation of a surfactant composition comprising N-methyl polyhydroxy fatty acid amide and N-alkyl (C3-C8) polyhydroxy fatty acid amide comprises mixing N-methyl polyhydroxy fatty acid amine and N-alkyl (C3-C8) polyhydroxy fatty acid amine to form a mixture. The mixture is reacted with a fatty acid ester reactant in the presence of a base catalyst and, optionally, in the presence of a reaction solvent. Unreacted N-alkoxyamino polyol is acylated with an acid anhydride at a temperature in the range of from 50.degree. C. to 85.degree. C. The weight ratio of N-methyl polyhydroxy fatty acid amide to N-alkyl (C3-C8) polyhydroxy fatty acid amide in the surfactant composition is from 25:1 to 1:1.
    Type: Grant
    Filed: April 19, 1996
    Date of Patent: May 12, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Jean-Pol Boutique, Patrick Firmin A. Delplancke
  • Patent number: 5741916
    Abstract: The present invention deals with the certain novel alkanolamides which are prepared by the reaction of an alkanolamie and meadowfoam fatty, methyl ester or triglyceride. These materials are useful as cosmetic ingredients as additives to shampoo systems where outstanding liquidity, resistance to oxidation, and minimal odor variation are required.
    Type: Grant
    Filed: July 31, 1996
    Date of Patent: April 21, 1998
    Assignee: Fan Tech Ltd.
    Inventor: Anthony J. O'Lenick, Jr.
  • 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: 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: 5665778
    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: October 12, 1994
    Date of Patent: September 9, 1997
    Assignee: L'Oreal
    Inventors: Didier Semeria, Michel Philippe, Claude Mahieu
  • 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: 5641495
    Abstract: A skin cosmetic causing little irritation and having an excellent moisturizing effect which contains the following components (A), (B) and (C):(A) a ceramide or a pseudoceramide represented by the following formula (1) or (2): ##STR1## wherein R.sup.1 and R.sup.2 represent each a C.sub.9 to C.sub.39 hydrocarbon group; and R.sup.3 and R.sup.4 represent each H, a phosphate residue, a sulfate residue, etc.;(B) a dicarboxylic acid; and(C) a salt of a dicarboxylic acid.
    Type: Grant
    Filed: October 17, 1995
    Date of Patent: June 24, 1997
    Assignee: Kao Corporation
    Inventors: Yoji Jokura, Toshio Uesaka, Seiji Honma, Yuri Kato, Koichi Ishida
  • Patent number: 5618955
    Abstract: Pure polyunsaturated fatty acid amides and their derivatives. These synthcally produced compounds are able to mimic naturally occuring anandamides in the brain and bind the cannabinoid receptor. The compounds exhibit physiological activity and are useful as active ingredients in pharmaceutical compositions for the treatment of inflammation, migraines, spasticity activity, glaucoma, multiple sclerosis. The active compounds can be provided in isotope-tagged form.
    Type: Grant
    Filed: July 26, 1995
    Date of Patent: April 8, 1997
    Assignee: Yissum Research Development Company of the Hebrew University of Jerusalem
    Inventors: Raphael Mechoulam, Aviva Beuer, Lemir Hanus, William A. Devane
  • Patent number: 5616746
    Abstract: The invention is characterized by the use in cosmetic compositions of one or more lipophilic derivatives of amino deoxyalditols corresponding to the general formula: ##STR1## in which: R.sup.1 is a saturated linear C.sub.14 -C.sub.40 aliphatic radical;R.sup.2 is a hydrogen atom or a linear C.sub.1 -C.sub.6 alkyl radical;X is an oxygen atom or a methylene radical; andn is an integer from 1 to 5;with the proviso that when X is a methylene radical R.sup.1 contains from 19 to 39 carbon atoms.Application to the preparation of cosmetic compositions for the treatment of keratinous substances and for buccodental hygiene.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 1, 1997
    Assignee: L'Oreal
    Inventors: Claude Mahieu, Didier Semeria, Dani ele Cauwet, Guy Vanlerberghe
  • 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: 5543431
    Abstract: A compound having the formula ##STR1## which is an anti-fungal agent is described. The producing organism Colletotricum accutatum is also described, along with a method of production.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: August 6, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Evon A. Bolessa, Robert E. Schwartz, Gerald F. Bills, Robert A. Giacobbe, Fernando Pelaez Perez, Angeles Cabello Arroyo, Teresa Diez Matas, Isabel Martin Fernandez, Francisca Vicente Perez, Suzanne M. Mandala, Deborah L. Zink, Rosemary Thornton, John R. Thompson, James E. Curotto
  • 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: 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: 5512699
    Abstract: Poly polyhydroxy fatty acid amide compounds and laundry, cleaning, fabric and personal care compositions comprising these compounds.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: April 30, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Daniel S. Connor, Yi-Chang Fu, Jeffrey J. Scheibel
  • Patent number: 5461071
    Abstract: A compound having the formula ##STR1## which is an anti-fungal agent is described. The producing organism Colletotricum accutatum is also described, along with a method of production.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: October 24, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Evon A. Bolessa, Robert E. Schwartz, Gerald F. Bills, Robert A. Giacobbe, Fernando Pelaez Perez, Angeles Cabello Arroyo, Teresa Diez Matas, Isabel Martin Fernandez, Francisca Vincente Perez, Suzanne M. Mandala, Deborah L. Zink, Rosemary Thornton, John R. Thompson, James E. Curotto
  • Patent number: 5415855
    Abstract: Modified ceramides are defined, together with their synthesis and compositions comprising them for topical application to human skin, hair and nails. The modified pseudoceramides have a structure: ##STR1## and an approximate summary is that R and R.sup.1 are aliphatic hydrocarbon, A is CH.sub.2, CHOR.sup.2, CH.dbd.CH or CHOY, and at least one of R.sup.2, R.sup.3 and R.sup.4 is sulphate, phosphate or similar. The presence of phosphate or sulphate facilitates skin absorption, after which the phosphate or sulphate is removed by enzymes present in vivo.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: May 16, 1995
    Assignee: Elizabeth Arden Co., Division of Conopco, Inc.
    Inventors: Peter Critchley, Susan E. Kirsch, Anthony V. Rawlings, Ian R. Scott
  • Patent number: 5338487
    Abstract: An improved process for manufacturing a linear glucamide surfactant comprises reacting an N-alkylglucamine, e.g., N-methylglucamine, a fatty ester, e.g., coconut methyl ester and a catalyst selected from trilithium phosphate, trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate, tetrapotassium pyrophosphate, pentasodium tripolyphosphate, pentapotassium tripolyphosphate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, disodium tartrate, dipotassium tartrate, sodium potassium tartrate, trisodium citrate, tripotassium citrate, sodium basic silicates, potassium basic silicates, sodium basic aluminosilicates, potassium basic aluminosilicates and mixtures thereof.
    Type: Grant
    Filed: January 26, 1993
    Date of Patent: August 16, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Daniel S, Connor, Jeffrey J. Scheibel, Ju-Nan Kao
  • Patent number: 5338486
    Abstract: Improved process for manufacturing a linear glucamide surfactant comprising reacting an N-alkylglucamine, e.g., N-methylglucamine, a fatty ester, e.g., coconut methyl ester and a catalyst at high concentration selected from trilithium phosphate, trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate, tetrapotassium pyrophosphate, pentasodium tripolyphosphate, pentapotassium tripolyphosphate, lithium carbonate, sodium carbonate, potassium carbonate, disodium tartrate, dipotassium tartrate, sodium potassium tartrate, trisodium citrate, tripotassium citrate, sodium basic silicates, potassium basic silicates, sodium basic aluminosilicates, potassium basic aluminosilicates and mixtures thereof.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: August 16, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Daniel S. Connor, Jeffrey J. Scheibel, Ju-Nan Kao
  • 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: 5312934
    Abstract: Polyhydroxy fatty acid amide nonionic surfactants are converted in high yields to their sulfated analog surfactants using an SO.sub.3 /pyridine complex as a sulfating agent. Thus, C.sub.12 -C.sub.18 N-methyl glucamide is sulfated in methylene chloride or pyridine solvent to form the corresponding sulfated glucamide in yields of 80% or higher.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: May 17, 1994
    Assignee: The Procter & Gamble Company
    Inventor: James C. Letton
  • 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: 5221757
    Abstract: An amide derivative represented by the following general formula (II): ##STR1## (wherein R.sup.3 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group carrying 10 to 40 carbon atoms; R.sup.4 represents a straight-chain or branched hydrocarbon group carrying 3 to 39 carbon atoms; and R.sup.5 represents a hydrogen atom, a straight-chain or branched, saturated or unsaturated hydrocarbon group carrying 10 to 40 carbon atoms or an acyl group); and a dermatologic preparation containing the same.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: June 22, 1993
    Assignee: Kao Corporation
    Inventors: Yukihiro Ohashi, Mituo Suda, Shinji Yano, Akira Kawamata, Minehiro Okuda, Genji Imokawa
  • 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: 5194639
    Abstract: Polyhydroxy fatty acid amide materials are prepared from reactants such as N-methylglucamine and fatty acid esters in the presence of hydroxy solvents. Polyhydroxy fatty acid amide detersive surfactants are secured. By-product and color formation are minimized.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: March 16, 1993
    Assignee: The Procter & Gamble Company
    Inventors: Daniel S. Connor, Jeffrey J. Scheibel, Roland G. Severson
  • Patent number: 5108661
    Abstract: The present invention relates to a process for the preparation of fatty diethanolamides with low diethanolamine content, characterized in that the raw product obtained by conventional reaction between the diethanolamine and said fatty acids or their derivatives, is subjected to an acylation reaction.It also relates to the products obtained according to this said process and to their use in formulations containing foaming agents.
    Type: Grant
    Filed: January 19, 1990
    Date of Patent: April 28, 1992
    Assignee: Societe d'Exploitation de Produits pour les Industries Chimiques S.E.P.O.I.C.
    Inventors: Jean-Pierre Boiteux, Bernard Brancq, Nelly Lecocu, Frederic Loussayre