Hydroxyalkyl Substituent On The Amido Nitrogen Patents (Class 554/66)
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Patent number: 5869711Abstract: 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: GrantFiled: April 5, 1996Date of Patent: February 9, 1999Assignee: L'OrealInventors: Michel Philippe, Bernadette Luppi, Didier Semeria
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Patent number: 5863945Abstract: 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: GrantFiled: November 24, 1997Date of Patent: January 26, 1999Assignee: Kao CorporationInventors: Koichi Murayama, Masahide Hoshino, Hiroshi Kusuoku, Minoru Nagai, Kiyoko Sugino
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Patent number: 5760258Abstract: 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: GrantFiled: August 8, 1996Date of Patent: June 2, 1998Assignee: Hoechst AktiengesellschaftInventor: Bernd Papenfuhs
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Patent number: 5753707Abstract: 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: GrantFiled: September 6, 1996Date of Patent: May 19, 1998Assignee: Kao CorporationInventors: Masahide Hoshino, Hiroshi Kusuoku, Tadashi Hase, Atsuko Otsuka, Ichiro Tokimitsu, Akira Yamamuro, Yoshiya Sugai, Koji Yoshino, Youichi Arai, Shinichi Meguro
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Patent number: 5750748Abstract: 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: GrantFiled: April 19, 1996Date of Patent: May 12, 1998Assignee: The Procter & Gamble CompanyInventors: Jean-Pol Boutique, Patrick Firmin A. Delplancke
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Patent number: 5741916Abstract: 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: GrantFiled: July 31, 1996Date of Patent: April 21, 1998Assignee: Fan Tech Ltd.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5728852Abstract: 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: GrantFiled: August 8, 1996Date of Patent: March 17, 1998Assignee: KAO CorporationInventors: Kenichi Nishikawa, Kazuhito Miyoshi, Yukiko Oshima, Hiroyuki Imoto
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Patent number: 5723673Abstract: 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: GrantFiled: June 7, 1995Date of Patent: March 3, 1998Assignee: The Procter & Gamble CompanyInventors: 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
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Patent number: 5688978Abstract: 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: GrantFiled: May 12, 1995Date of Patent: November 18, 1997Assignee: Witco CorporationInventors: Ginette Lefebvre, Line Fiquet
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Patent number: 5665778Abstract: 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: GrantFiled: October 12, 1994Date of Patent: September 9, 1997Assignee: L'OrealInventors: Didier Semeria, Michel Philippe, Claude Mahieu
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Patent number: 5646318Abstract: 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: GrantFiled: April 26, 1995Date of Patent: July 8, 1997Assignee: Akzo Nobel nvInventors: Maurice Dery, Nils Brolund
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Patent number: 5641495Abstract: 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: GrantFiled: October 17, 1995Date of Patent: June 24, 1997Assignee: Kao CorporationInventors: Yoji Jokura, Toshio Uesaka, Seiji Honma, Yuri Kato, Koichi Ishida
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Patent number: 5618955Abstract: 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: GrantFiled: July 26, 1995Date of Patent: April 8, 1997Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventors: Raphael Mechoulam, Aviva Beuer, Lemir Hanus, William A. Devane
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Patent number: 5616746Abstract: 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: GrantFiled: June 5, 1995Date of Patent: April 1, 1997Assignee: L'OrealInventors: Claude Mahieu, Didier Semeria, Dani ele Cauwet, Guy Vanlerberghe
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Patent number: 5571934Abstract: 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: GrantFiled: August 1, 1995Date of Patent: November 5, 1996Assignee: Hoechst AGInventors: Bernd Papenfuhs, Reinhard Vybiral
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Patent number: 5543431Abstract: 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: GrantFiled: May 24, 1995Date of Patent: August 6, 1996Assignee: 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
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Patent number: 5539134Abstract: 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: GrantFiled: April 24, 1995Date of Patent: July 23, 1996Assignee: BASF AktiengesellschaftInventors: Beate Strecker, Helmut Wolf, Gerhard Wolf, Alfred Oftring, Hans-Heinrich Bechtolsheimer, Dieter Hertel
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Patent number: 5523431Abstract: 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: GrantFiled: October 29, 1993Date of Patent: June 4, 1996Assignees: Berol Nobel AB, Castrol Ltd.Inventor: Rolf Skold
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Patent number: 5512699Abstract: Poly polyhydroxy fatty acid amide compounds and laundry, cleaning, fabric and personal care compositions comprising these compounds.Type: GrantFiled: November 21, 1994Date of Patent: April 30, 1996Assignee: The Procter & Gamble CompanyInventors: Daniel S. Connor, Yi-Chang Fu, Jeffrey J. Scheibel
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Patent number: 5461071Abstract: 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: GrantFiled: October 21, 1994Date of Patent: October 24, 1995Assignee: 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
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Patent number: 5415855Abstract: 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: GrantFiled: June 22, 1993Date of Patent: May 16, 1995Assignee: Elizabeth Arden Co., Division of Conopco, Inc.Inventors: Peter Critchley, Susan E. Kirsch, Anthony V. Rawlings, Ian R. Scott
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Patent number: 5338487Abstract: 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: GrantFiled: January 26, 1993Date of Patent: August 16, 1994Assignee: The Procter & Gamble CompanyInventors: Daniel S, Connor, Jeffrey J. Scheibel, Ju-Nan Kao
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Patent number: 5338486Abstract: 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: GrantFiled: January 21, 1993Date of Patent: August 16, 1994Assignee: The Procter & Gamble CompanyInventors: Daniel S. Connor, Jeffrey J. Scheibel, Ju-Nan Kao
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Patent number: 5318727Abstract: 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: GrantFiled: August 14, 1991Date of Patent: June 7, 1994Assignee: Kao CorporationInventors: Yasuki Ohtawa, Makoto Kubo, Hiroyuki Imoto, Takashi Matsuo, Kazuyuki Yahagi, Koshiro Sotoya
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Patent number: 5312934Abstract: 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: GrantFiled: November 30, 1992Date of Patent: May 17, 1994Assignee: The Procter & Gamble CompanyInventor: James C. Letton
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Patent number: 5298636Abstract: 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: GrantFiled: September 23, 1992Date of Patent: March 29, 1994Assignee: The Procter & Gamble CompanyInventors: Daniel S. Connor, Mark Hsiang-Kuen Mao
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Patent number: 5221757Abstract: 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: GrantFiled: November 20, 1991Date of Patent: June 22, 1993Assignee: Kao CorporationInventors: Yukihiro Ohashi, Mituo Suda, Shinji Yano, Akira Kawamata, Minehiro Okuda, Genji Imokawa
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Patent number: 5208355Abstract: 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: GrantFiled: May 1, 1991Date of Patent: May 4, 1993Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.Inventor: Ian R. Scott
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Patent number: 5194639Abstract: 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: GrantFiled: September 6, 1991Date of Patent: March 16, 1993Assignee: The Procter & Gamble CompanyInventors: Daniel S. Connor, Jeffrey J. Scheibel, Roland G. Severson
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Patent number: 5108661Abstract: 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: GrantFiled: January 19, 1990Date of Patent: April 28, 1992Assignee: 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