Quaternary Ammonium Containing Patents (Class 554/52)
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Patent number: 5834516Abstract: The present invention deals with the composition of matter and the utilization of certain novel meadowfoam based betaine compounds. These materials are useful in personal care applications.Type: GrantFiled: May 1, 1997Date of Patent: November 10, 1998Assignee: Fan Tech LtdInventor: Anthony J. O'Lenick, Jr.
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Patent number: 5830870Abstract: Disclosed herein are inhibitors of the multicatalytic protease enzyme which are represented by the general formula: ##STR1## Constituent members and preferred constituent members are disclosed herein. Methodologies for making and using the disclosed compounds are also set forth herein.Type: GrantFiled: December 4, 1996Date of Patent: November 3, 1998Assignee: Cephalon, Inc.Inventors: Mohamed Iqbal, James L. Diebold, Robert Siman, Sankar Chatterjee, James C. Kauer
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Patent number: 5756784Abstract: An amide represented by the following formula (1): ##STR1## wherein R.sup.1 and R.sup.2 are C1-C24 alkyl, etc.; B is C2-C10 alkylene, etc.; A.sup.1 and A.sup.2 are C1-C6 alkylene, etc.; Y.sup.1 and Y.sup.2 are ##STR2## wherein R.sup.3, R.sup.4, and R.sup.5 are C1-C4 alkyl, etc., and X.sup.1 is halogen; or a salt of the amide and detergent compositions containing the amide or salt are mild to the skin or hair, provide a pleasant sensation to the skin or hair, and have excellent latherability and emulsion stability. These compounds are useful as components of various detergents and cosmetic compositions, emulsifiers, and conditioners.Type: GrantFiled: May 8, 1996Date of Patent: May 26, 1998Assignee: Kao CorporationInventors: Mitsuru Uno, Tetsuya Miyajima, Tomohito Kitsuki, Katsumi Kita
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Patent number: 5756785Abstract: The present invention deals with the composition of matter and the utilization of certain novel guerbet based betaine compounds. These materials are useful in personal care applications.Type: GrantFiled: March 21, 1997Date of Patent: May 26, 1998Assignee: Lambent Technologies, Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5750492Abstract: Cationic surfactant compound comprising, in the form of a quaternary ammonium salt, a product of condensation between, on the one hand a fraction of saturated or unsaturated fatty acids, or of derivatives of said acids chosen from the group comprising esters, anhydrides and acid chlorides, and on the other hand at least one tertiary amine, characterized in that, in combination:the alkyl chains of the tertiary amine together contain from 4 to 12 carbon atomsthe alkyl chains of the tertiary amine together contain from 1 to 4 functions each chosen from the group comprising hydroxyl and amine functionsthe fatty acids fraction/tertiary amine mole ratio is between 1.85 and 1.40the fatty acids each possess a hydrocarbon chain in which the number of carbon atoms is between 5 and 23.Type: GrantFiled: June 10, 1997Date of Patent: May 12, 1998Assignee: Stepan EuropeInventors: Jean-Pierre Contet, Stephane Courdavault Duprat, Yvan Storet, Jean-Francois Vindret
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Patent number: 5741915Abstract: The present invention deals with the composition of matter and the utilization of certain novel meadowfoam based betaine compounds. These materials are useful in personal care applications.Type: GrantFiled: January 13, 1997Date of Patent: April 21, 1998Assignee: Fan Tech Ltd.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5734069Abstract: Compounds of the formula R--?C(O)O(CH.sub.2).sub.1-5 !.sub.0-1 --C(O)NH(CH.sub.2).sub.2-5 --N(R.sup.2)--(CH.sub.2).sub.2-5 --OC(O)R.sup.1 wherein R and R.sup.1 are each C.sub.8 -C.sub.22 alkyl or alkenyl and R.sup.2 is C.sub.1 -C.sub.3 alkyl or hydroxyalkyl, benzyl, or --C.sub.2 H.sub.4 OC(O)R.sup.4 wherein R.sup.4 is C.sub.8 -C.sub.22 alkyl or alkenyl, and acid salts and derivatives of such compounds quaternized with methyl, ethyl or benzyl, exhibit useful fabric softening and static reduction properties, as well as biodegradability.Type: GrantFiled: September 14, 1994Date of Patent: March 31, 1998Assignee: Sherex Chemical Co., Inc.Inventors: Christopher Joseph Toney, Floyd D. Friedli
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Patent number: 5681972Abstract: 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: GrantFiled: March 30, 1995Date of Patent: October 28, 1997Assignee: Witco Surfactants GmbHInventors: Ingo Hamann, Hans-Jurgen Kohle, Winfried Wehner
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Patent number: 5637743Abstract: Cationic surfactant compound comprising, in the form of a quaternary ammonium salt, a product of condensation between, on the one hand a fraction of saturated or unsaturated fatty acids, or of derivatives of said acids chosen from the group comprising esters, anhydrides and acid chlorides, and on the other hand at least one tertiary amine, characterized in that, in combination:the alkyl chains of the tertiary amine together contain from 4 to 12 carbon atomsthe alkyl chains of the tertiary amine together contain from 1 to 4 functions each chosen from the group comprising hydroxyl and amine functionsthe fatty acids fraction/tertiary amine mole ratio is between 1.85 and 1.40the fatty acids each possess a hydrocarbon chain in which the number of carbon atoms is between 5 and 23.Type: GrantFiled: May 22, 1995Date of Patent: June 10, 1997Assignee: Stepan EuropeInventors: Jean-Pierre Contet, Stephane C. Duprat, Lionel Godefroy, Paul Nivollet, Didier Ray, Yvan Storet, Jean-Francois Vindret
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Patent number: 5578234Abstract: The present invention relates to dryer-activated fabric softening compositions and articles, having improved antistatic and/or softening effects, for use in an automatic clothes dryer, especially those comprising, as essential ingredients: (A) fabric softener consisting essentially of: (1) from about 5% to about 95% of preferably biodegradable quaternary ammonium compound selected from the group consisting of the compounds of Formulas I, II, III, and mixtures thereof; (2) from 0% to about 95% highly ethoxylated and/or propoxylated, preferably at least 5 ethylene oxide (EO) and/or propylene oxide (PO) groups per molecule, sugar derivative containing at least one long hydrophobic moiety per molecule; and (3) from 0% to about 95% of carboxylic acid salt of tertiary amine; and (B) from about 1% to about 15%, unsaturated fatty acid having an IV of from about 3 to about 60. The amount of (A) present is at least sufficient to provide softening and/or antistatic effects.Type: GrantFiled: October 10, 1995Date of Patent: November 26, 1996Assignee: The Procter & Gamble CompanyInventors: Alessandro Corona, III, Clyde D. Palmer, John R. Rusche, Stephanie Lin-Lin Sung
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Patent number: 5550262Abstract: Disclosed herein are inbibitors of the multicatalytic protease enzyme which are represented by the general formula: ##STR1## Constituent members and preferred constituent members are disclosed herein. Methodologies for making and using the disclosed compounds are also set forth herein.Type: GrantFiled: November 14, 1994Date of Patent: August 27, 1996Assignee: Cephalon, Inc.Inventors: Mohamed Iqbal, James L. Diebold, Robert Siman, Sankar Chatterjee, James C. Kauer
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Patent number: 5523432Abstract: Quaternary ammonium salts of fatty acid hydroxyalkanesulfonic acids are made by reacting a hydroxyalkanesulfonic acid of the formula (I):HO--(C.sub.n H.sub.2n)--SO.sub.3 H (I):wherein n=2 to 4 with a fatty acid having from 6 to 18 carbon atoms at a temperature range of from about 60.degree. C. to about 120.degree. C. and at a reduced pressure followed b reaction with an amine in an organic solvent.Type: GrantFiled: April 7, 1994Date of Patent: June 4, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hans-Christian Raths, Rainer Rueben, Manfred Biermann, Timothy J. Cassady
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Patent number: 5508454Abstract: 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: GrantFiled: August 4, 1994Date of Patent: April 16, 1996Assignee: Societe d'Exploitation de Produits pour les Industries Chimiques -SEPPICInventors: Bernard Brancq, Jean-Pierre Boiteux
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Patent number: 5491245Abstract: A method for the synthesis of amphoteric surfactants by the reaction of amines with chloroacetic acid or its salts in aqueous solution at an elevated temperature, consists of reacting compounds of the general formula ##STR1## with chloroacetic acid at temperatures ranging from 115.degree. to 180.degree. C., until the chloroacetic acid content is less than 10 ppm.Type: GrantFiled: March 15, 1994Date of Patent: February 13, 1996Assignee: Th. Goldschmidt AGInventors: Burghard Gruning, Christian Weitemeyer
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Patent number: 5476597Abstract: To provide an aqueous fabric softener composition, which is excellent in softening performance, elasticity and storage stability, and a quaternary ammonium salt which is useful as a softening base of this composition and nondetrimental to the natural environment because of its excellent biodegradability and a process for the preparation of this salt.The aqueous fabric softener composition of the present invention comprises from 3 to 40% by weight of a quaternary ammonium salt represented by the following formula (I), and water: ##STR1## wherein R.sup.1 and R.sup.2 represent each a C.sub.1-4 alkyl group, etc.; R.sup.3 and R.sup.4 represent each a C.sub.7-35 alkyl group, etc.; and X.sup.- represents an anion group.Type: GrantFiled: September 8, 1994Date of Patent: December 19, 1995Assignee: Kao CorporationInventors: Yushi Sakata, Junichi Inokoshi, Tohru Katoh, Osamu Tachizawa, Uichiro Nishimoto, Yasuki Ohtawa, Masaaki Yamamura
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Patent number: 5470992Abstract: 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: GrantFiled: March 14, 1994Date of Patent: November 28, 1995Assignee: Th. Goldschmidt AGInventors: Burghard Gruning, Willi Foitzik, Christian Weitemeyer, Hans-Dieter Kaseborn
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Patent number: 5464565Abstract: The invention relates to a process for the preparation of highly concentrated free-flowing aqueous solutions of betaines, which is characterized in that at least one of the compounds of the general formula (I) ##STR1## is added to the reaction mixture before or during the quaternization reaction; wherein R, R.sup.1, R.sup.2, are each C.sub.1 -C.sub.10 alkyl, optionally substituted with hydroxyl, and n is 1-3.Type: GrantFiled: October 11, 1994Date of Patent: November 7, 1995Assignee: Witco Surfactants GmbHInventors: Ingo Hamann, Hans-Jurgen Kohle, Winfried Wehner
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Patent number: 5444154Abstract: The present invention relates to a series of novel crosslinked polymers. The compounds of the present invention are prepared by the reaction of chloracetic acid with a pendant hydroxyl group which is present on a polyoxyalkylene polymer, followed by the reaction of the halo-ester with a protein or amino acid to give a crosslinked protein compound. In a preferred embodiment the polyoxyalkylene glycol has been prepared by the reaction of both ethylene oxide and propylene oxide. In a more preferred embodiment, the ethylene oxide is at the terminal portion of the molecule and the propylene oxide is in the center. The proteins of the present invention plate out on the surface of hair skin and once dry act as humectants, trapping moisture to the hair. This results in hair which is fuller, has less static and is cosmetically more appealing. This combination of properties makes these polymers ideally suited for use in personal care applications.Type: GrantFiled: June 15, 1994Date of Patent: August 22, 1995Assignee: Siltech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5371250Abstract: 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: GrantFiled: September 13, 1993Date of Patent: December 6, 1994Assignee: Hoechst AktiengesellschaftInventors: Hubert Seitz, Reinhard Vybiral
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Patent number: 5354906Abstract: 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: GrantFiled: February 12, 1993Date of Patent: October 11, 1994Assignee: Th. Goldschmidt AGInventors: Christian Weitemeyer, Willi Foitzik, Hans-Dieter Kaseborn, Burghard Gruning, Uwe Begoihn
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Patent number: 5344949Abstract: Surface active anion-cation complexes are synthesized where an organic or organosilicon compound with at least one epoxide group is reacted with a quaternary ammonium hydrogen sulfite of the general formulaHN.sup.+ (R.sup.1).sub.3 SO.sub.3 H.sup.- IwhereinR.sup.1 within the molecule is the same or different and can be(1) an alkyl or hydroxyalkyl group with 1 to 18 carbon atoms,(2) a phenyl group, or(3) a group of the formula C.sub.n H.sub.2n+1 CONH--(CH.sub.2).sub.m --, in which n can be a number from 7 to 17 and m is 2 or 3,in the presence of a polar solvent in such amounts so that the molar ratio of the epoxide group to HN.sup.+ (R.sup.1).sub.3 SO.sub.3 H.sup.- is 2:1.Type: GrantFiled: July 14, 1993Date of Patent: September 6, 1994Assignee: Th. Goldschmidt AGInventors: Gotz Koerner, Klaus-Dieter Klein, Dietmar Schaefer
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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: 5298656Abstract: The present invention relates to a series of novel quaternary polymers and an intermediate useful in it's preparation. The compounds of the present invention are prepared by the reaction of chloracetic acid with a pendant hydroxyl group which is present on a polyoxyalkylene polymer, followed by the reaction of the halo-ester with a tertiary amine to give a quaternary compound. In a preferred embodiment the polyoxyalkylene glycol has been prepared by the reaction of both ethylene oxide and propylene oxide. In a more preferred embodiment, the ethylene oxide is at the terminal portion of the molecule and the propylene oxide is in the center.Type: GrantFiled: June 19, 1992Date of Patent: March 29, 1994Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5292942Abstract: A process is described for the preparation of aqueous solutions of betaines of the formula ##STR1## in which: R.sup.1 is an alkyl radical having 6 to 22 carbon atoms or is a radical of the formula R'CONH(CH.sub.2).sub.z --, in which R' has the meaning of R.sup.1 and z is 2, 3 or 4, R.sup.2 is an alkyl radical having 1 to 4 carbon atoms or is a radical of the formula --(CH.sub.2).sub.m --OH, in which m is 1, 2 or 3, R.sup.3 is an alkyl radical having 1 to 4 carbon atoms or is a radical of said formula --(CH.sub.2).sub.m --OH and y is 1, 2 or 3. The aqueous betaine solutions are prepared by quaternization of the corresponding tertiary amines with an .omega.-halocarboxylic acid and with an alkali metal hydroxide in the aqueous phase. The quaternization is carried out continuously in two or three stirred tanks arranged in a cascade, defined process characteristics being maintained in each tank. Using the novel process, aqueous betaine solutions are obtained in high yield and purity in a simple manner.Type: GrantFiled: April 2, 1993Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Rudolf Aigner, Guillermo Maier, Rainer Muller, Hubert Seitz
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Patent number: 5284650Abstract: A process is disclosed for making substantially solvent free quaternary ammonium compounds using fatty acids, amines and quaternizing agents without side reactions that would produce esters of fatty acids. A relatively small amount of a water-alcohol solvent is used in the quaternizing reaction after which a fatty acid is added and the solvent removed by sparging and/or vacuum.Type: GrantFiled: November 5, 1992Date of Patent: February 8, 1994Assignee: Sherex Chemical Co., Inc.Inventor: David E. Whittlinger
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Patent number: 5223628Abstract: A process is disclosed for making substantially solvent free quaternary ammonium compounds using fatty acids, amines and quaternizing agents without side reactions that would produce esters of fatty acids. A relatively small amount of a water-alcohol solvent is used in the quaternizing reaction after which a fatty acid is added and the solvent removed by sparging and/or vacuum.Type: GrantFiled: November 7, 1991Date of Patent: June 29, 1993Assignee: Sherex Chemical Company, Inc.Inventor: David E. Whittlinger
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Patent number: 5221794Abstract: The invention relates to a method of producing a mixture of a quaternary ammonium compound, fatty acid, fatty acid ester and tertiary amine salt in situ which is a highly functional mixture that is manufactured in a single step reaction whereby quaternization is completed without the aid of solvents, especially flammable solvents. The single step reaction process eliminates separate blending of individual components. The compositions obtained can be used as fabric softeners, in modified clays, as hair treating compounds and as disinfectants.Type: GrantFiled: November 7, 1991Date of Patent: June 22, 1993Assignee: Sherex Chemical Company, Inc.Inventors: Jeannene A. Ackerman, Michael Miller, David E. Whittlinger
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Patent number: 5204375Abstract: Lipophilic amphoteric surface active compositions exhibiting remarkable W/O emulsifying property and good stabililty against oxidation, comprising betaines having the general formula ##STR1## wherein R.sub.1 --CO is an acyl radical of estolides, R.sub.2 is an alkylene group having 1 to 3 carbon atoms and n is an integer from 1 to 3.Type: GrantFiled: January 14, 1992Date of Patent: April 20, 1993Assignee: Itoh Seiyu Kabushiki KaishaInventors: Susumu Kusakawa, Yoshiyuki Itoh, Yuka Saigusa
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Patent number: 5182407Abstract: The present invention relates to the compounds of formula (I): ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, denote a methyl or ethyl radical;R.sub.3 denotes a methyl, ethyl or hydroxyethyl radical;A denotes a ##STR2## radical or ##STR3## R denotes H or CH.sub.3 ; X denotes Cl.sup.-, BR.sup.-, I.sup.-, CH.sub.3 OSO.sub.3.sup.-, CH.sub.3 SO.sub.3.sup.-, ##STR4## p and q, which are identical or different, denote integers such that 1.ltoreq.p.ltoreq.15, 0.ltoreq.q.ltoreq.13 and 2.ltoreq.p+q.ltoreq.20;n denotes an integer equal to 2 or 3;m denotes 0 or 1, and m+q.noteq.0;as well as the salts from neutralization by bases, their preparation process and their utilization as an additive in compositions for treatment of keratinous materials.Type: GrantFiled: July 17, 1991Date of Patent: January 26, 1993Assignee: L'OrealInventor: Henri Sebag
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Patent number: 5124081Abstract: Amphiphilic lipid compound having the formula: ##STR1## in which: R.sub.1 denotes a C.sub.7 -C.sub.21 alkyl or alkenyl radical,R.sub.2 denotes a saturated or unsaturated C.sub.7 -C.sub.31 hydrocarbon radical,COA denotes a group chosen from the following groups:a) COOM, M being H, Na, K, NH.sub.4 or a substituted ammonium ion derived from an amine,b) ##STR2## B being a radical derived from mono- or polyhydroxylated primary or secondary amines and R denoting a hydrogen atom or a methyl, ethyl or hydroxyethyl radical,c) ##STR3## Q denoting a substituted aminoalkyl or ammonioalkyl radical and R having the meaning indicated for b), andd) COOZ, Z representing the residue of a C.sub.3 -C.sub.7 polyol, and a process for its preparation.Cosmetic or dermopharmaceutical composition comprising the said compound and especially an aqueous dispersion of liposomes.Type: GrantFiled: June 24, 1986Date of Patent: June 23, 1992Assignee: L'OrealInventors: Guy Vanlerberghe, Alexandre Zysman, Henri Sebag