Amine Oxides Patents (Class 564/297)
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Patent number: 5756000Abstract: This invention provides perfluoro(alkoxycycloalkane) carbonyl fluoride compounds wherein, pendant from the fluorinated ring, are from 2 to 5 perfluoroalkoxy groups having from 1 to 4, preferably 1 to 2, carbon atoms with the proviso that when one or more of the perfluoroalkoxy groups contain from 3 to 4 carbon atoms, there are no more than 3 pendant groups.In yet another aspect, this invention provides aqueous film-forming foam (AFFF) compositions comprising one or more perfluoro(alkoxycycloalkane) carbonyl group-containing surfactants and one or more water-soluble fluorine-free surfactants selected from the group consisting of nonionic hydrocarbon-containing surfactants with a hydrophilic-lipophilic balance (HLB) value greater than or equal to about 10 and ionic hydrocarbon-containing surfactants having a carbon chain length containing inclusively from about 6 to about 10 carbon atoms.Type: GrantFiled: February 6, 1996Date of Patent: May 26, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: John C. Hansen, George G. I. Moore, Stephen D. Polson, Patricia M. Savu, Richard M. Stern
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Patent number: 5710333Abstract: Process for the preparation of tertiary amine oxides by reaction of a tertiary amine with a compound which splits off oxygen. To avoid gel and foam formation, a portion of the amine oxide to be prepared is added before the start of this reaction.Type: GrantFiled: August 6, 1996Date of Patent: January 20, 1998Assignee: Hoechst AktiengesellschaftInventors: Georg Bader, Ramon Joglar Tamargo
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Patent number: 5710332Abstract: A method for the manufacture of N,N dialkylglycamine compounds of general formula R.sub.2 NR.sub.1 R.sub.3 (I) by reacting a secondary amine of general formula R.sub.2 NHR.sub.3 (II) in which R.sub.2 is a straight or branched chain alkyl or hydroxyalkyl group having from 1 to 4 carbon atoms and R.sub.3 is a residue from a monosaccharide, with an alkali metal or alkaline earth metal aliphatic sulphate, R.sub.1 SO.sub.4 M, in which R.sub.1 is a straight or branched chain alkyl or alkenyl group having from 8 to 24 carbon atoms.The betaine, suphobetaine and N-oxidised derivatives of (I) are provided for use as mild surfactants.Type: GrantFiled: July 12, 1996Date of Patent: January 20, 1998Assignee: Albright & Wilson LimitedInventors: Brynley Morris Phillips, Ajit Kumar, Alan Smithson
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Patent number: 5668281Abstract: A process for preparing a tertiary amine-N-oxide which comprises reacting a tertiary amine with a peroxide in the presence of a catalyst comprising an oxide containing silicon and titanium atoms. According to the process of the present invention, a tertiary amine-N-oxide can be obtained in a high yield, and since the catalyst can easily be separated from the reaction mixture, the tertiary amine-N-oxide can be obtained in a high purity without the contamination by the catalyst.Type: GrantFiled: January 19, 1996Date of Patent: September 16, 1997Assignee: Koei Chemical Co., Ltd.Inventors: Shinkichi Shimizu, Nanao Watanabe, Hideki Kuranishi
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Patent number: 5639880Abstract: A process for preparing amine oxides of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.30 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.1 -C.sub.30 -hydroxyalkyl, C.sub.1 -C.sub.30 -aminoalkyl, C.sub.2 -C.sub.30 -alkoxyalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -alkylaryl, C.sub.1 -C.sub.8 -alkyl-, C.sub.1 -C.sub.8 -alkoxy- or halogen-monosubstituted, -disubstituted, -trisubstituted, -tetrasubstituted or -pentasubstituted C.sub.3 -C.sub.12 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -alkylaryl, --[(CH.sub.2).sub.2 --O].sub.n --R.sup.4, --{[CH(CH.sub.3)CH.sub.2 ]--O}.sub.m --R.sup.5, or R.sup.1 and R.sup.2 are together an uninterrupted or oxygen-, nitrogen- or sulfur-interrupted C.sub.3 -C.sub.12 -alkylene diradical chainR.sup.4 and R.sup.5 are each C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, hydroxyl, --COR.sup.6 or --CH.sub.2 --COOR.sup.7, C.sub.3 -C.sub.12 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl or C.sub.7 -C.Type: GrantFiled: May 30, 1996Date of Patent: June 17, 1997Assignee: BASF AktiengesellschaftInventors: Ulrich Muller, Klemens Massonne, Karsten Eller, Michael Schulz
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Patent number: 5628941Abstract: The invention is concerned with a process for the production of cellulose moulded bodies. In this process, cellulose is first dissolved in an aqueous solution of a tertiary amine-oxide, in particular N-methylmorpholine-N-oxide (NMMO), to produce a mouldable cellulose solution. Second, the cellulose solution is molded and conducted into an aqueous precipitation bath, wherein the cellulose is precipitated, which produces a moulded body and a spent precipitation bath. Next, the spent precipitation bath is regenerated. This regenerated aqueous amine-oxide solution is re-used to dissolve cellulose, thereby repeating the process. In the above process, the repeated aqueous amine-oxide solution has a pH within certain defined limits.Type: GrantFiled: June 5, 1995Date of Patent: May 13, 1997Assignee: Lenzing AktiengesellschaftInventors: Wolfram Kalt, Heinrich Firgo, Johann Manner, Eduard Mulleder, Bruno Mangeng, Arnold Nigsch, Franz Schwenninger, Christoph Schrempf
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Patent number: 5621144Abstract: New compounds are described typically having the formula CH.sub.3 C(CH.sub.2 R).sub.3 or ZCH.sub.2 C(CH.sub.2 R).sub.3 where R is a fluorohydrocarbon or perfluorocarbon group, preferably containing 4-16 carbon atoms and more F atoms that H atoms. Z is a hydrophilic group which may make the compound self-emulsifiable. The compounds are useful as oxygen transport agents in vivo, for which purpose aqueous emulsions are used, as a blood substitute.Type: GrantFiled: January 9, 1995Date of Patent: April 15, 1997Assignee: Isis Innovation LimitedInventor: Stephen R. Cooper
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Patent number: 5523478Abstract: A method for the manufacture of N,N dialkylglycamine compounds of general formula R.sub.2 NR.sub.1 R.sub.3 (I) by reacting a secondary amine of general formula R.sub.2 NHR.sub.3 (II) in which R.sub.2 is a straight or branched chain alkyl or hydroxyalkyl group having from 1 to 4 carbon atoms and R.sub.3 is a residue from a monosaccharide, with an alkali metal or alkaline earth metal aliphatic sulphate, R.sub.1 SO.sub.4 M, in which R.sub.1 is a straight or branched chain alkyl or alkenyl group having from 8 to 24 carbon atoms.The betaine, suphobetaine and N-oxidised derivatives of (I) are provided for use as mild surfactants.Type: GrantFiled: November 16, 1994Date of Patent: June 4, 1996Assignee: Albright & Wilson LimitedInventors: Brynley M. Phillips, Ajit Kumar, Alan Smithson
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Patent number: 5498373Abstract: Amine oxide surfactants contaminated with nitrite are treated under acidic conditions with materials such as maleic acid and diethylenetriaminepentaacetate (DTPA) to reduce nitrite levels below 1 ppm. Thus, C.sub.12-13 dimethyl amine is oxidized with hydrogen peroxide in the presence of maleic acid and DTPA to reduce nitrite levels. The resulting nitrite-free amine oxide is employed in various detergent compositions.Type: GrantFiled: June 7, 1995Date of Patent: March 12, 1996Assignee: The Procter & Gamble CompanyInventors: Larry E. Miller, Gene P. Hawkins, Bernard G. Durham
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Patent number: 5498791Abstract: A synergistic mixture of a carbonate and/or bicarbonate with a phosphonate, especially an organoamino methylene phosphonate or an N-oxide thereof, inhibits or reduces nitrosamine contamination during preparation, storage and/or heating of products which are susceptible to contamination with nitrosamine.Type: GrantFiled: January 20, 1995Date of Patent: March 12, 1996Assignee: Albright & Wilson, LimitedInventors: Michael Blezard, Glyn R. Jones, Moharam Ghadimi
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Patent number: 5486315Abstract: An amine oxide having the formula: ##STR1## wherein the R.sub.1 groups are independently selected from C.sub.1 -C.sub.4 alkyl or alkoxy groups and R.sub.2 is a branched chain C.sub.11 -C.sub.16 alkyl group; a detersive composition containing such amine oxide with amphoteric surfactants and/or alkalizing agent; and the use of said composition for cleaning hard surfaces.Type: GrantFiled: May 20, 1994Date of Patent: January 23, 1996Assignee: Lonza Inc.Inventor: Chuen-Ing J. Tseng
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Patent number: 5466870Abstract: Amine oxide surfactants contaminated with nitrite are treated under acidic conditions with materials such as maleic acid and diethylenetriaminepentaacetate (DTPA) to reduce nitrite levels below 1 ppm. Thus, C.sub.12-13 dimethyl amine is oxidized with hydrogen peroxide in the presence of maleic acid and DTPA to reduce nitrite levels. The resulting nitrite-free amine oxide is employed in various detergent compositions.Type: GrantFiled: August 5, 1994Date of Patent: November 14, 1995Assignee: The Procter & Gamble CompanyInventors: Larry E. Miller, Gene P. Hawkins, Bernard G. Durham
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Patent number: 5431901Abstract: Selective isotopic-labeling of spin label compounds, used in electron spin resonance spectroscopy to detect, measure and monitor the presence of paramagnetic species, increases the sensitivity of the electron spin resonance technique in assays for paramagnetic species, such as the determination of oxygen tension in solution or in a biological sample, like a living organism. Spin label compounds, such as nitroxides, like 3-carbamoyl-2,2,5,5-tetramethyl-3-pyrroline-1-yloxyl (CTPO), are selectively, but not completely, isotopically-labeled, such as partially deuterated, to increase the sensitivity and reliability of assays employing electron spin resonance spectroscopic measurements.Type: GrantFiled: August 3, 1988Date of Patent: July 11, 1995Inventors: Howard J. Halpern, Beverly A. Teicher
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Patent number: 5409532Abstract: Amine-oxides of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are alkyl groups with 1 to 4 C-atoms, R.sub.3 is hydrogen, a hydroxyl group or an alkoxy group with 1 to 4 C-atoms and m and n are whole numbers which fulfil the conditions 1.ltoreq.m.ltoreq.8 and 0.ltoreq.n.ltoreq.4 respectively, with the proviso that n is not 0 if R.sub.3 is a hydroxyl group or an alkoxy group, can be used with advantage for the preparation of mouldable or spinnable cellulose solutions which have a reduced tendency to crystallise.Type: GrantFiled: January 21, 1993Date of Patent: April 25, 1995Assignee: Lenzing AktiengesellschaftInventors: Stephan Astegger, Dieter Eichinger, Heinz Falk, Gunter Teubl
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Patent number: 5359139Abstract: A tert-amine which contains an acid-activated color body precursor is treated to prevent it or a derivative thereof, e.g., an amine oxide, betaine, or quaternary ammonium compound, from turning pink when exposed to acidic conditions by contacting it with ascorbic acid.Type: GrantFiled: March 18, 1991Date of Patent: October 25, 1994Assignee: Albemarle CorporationInventors: Kim R. Smith, James E. Borland, Joe D. Sauer
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Patent number: 5292954Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a nonionic surfactant as the sole organic solvent, at least a portion of the nonionic surfactant being an alkylphenol ethoxylate or other compound corresponding to the formula Z[OC(Z')HCH.sub.2 ].sub.m OH in which Z is an alkylphenyl group wherein the alkyl group contains 4-30 carbons, Z' is hydrogen or an alkyl or hydroxyalkyl group containing 1-3 carbons, and m is an integer of 1-100. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.Type: GrantFiled: December 17, 1990Date of Patent: March 8, 1994Assignee: Ethyl CorporationInventors: James E. Borland, Joe D. Sauer, Kim R. Smith
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Patent number: 5292955Abstract: Novel perhydrates having utility as surfactants and bleaching agents are obtained by reacting an anhydrous amine oxide or an amine oxide monohydrate with hydrogen peroxide in such proportions as to provide a compound corresponding to the formula RR'R"NO.multidot.xH.sub.2 O.multidot.yH.sub.2 O.sub.2 in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons; x is 0 or 1; y is 1 or 2; and x+y is .ltoreq.2.Type: GrantFiled: June 22, 1992Date of Patent: March 8, 1994Assignee: Ethyl CorporationInventors: Kim R. Smith, James E. Borland, Joe D. Sauer
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Patent number: 5254735Abstract: A solid amine oxide is prepared by reacting a tert-amine with at least a stoichiometric amount of an aqueous hydrogen peroxide having a concentration of at least 50% by weight in the presence as the reaction medium of a normally gaseous material which (a) has a critical temperature <160.degree. C. and a critical pressure <12 MPa, (b) is in a liquefied, densified, or supercritical state in which it has a density of at least 0.1 g/cc, and (c) is present in an amount sufficient to maintain the reaction mixture stirrable throughout the reaction.Type: GrantFiled: May 4, 1992Date of Patent: October 19, 1993Assignee: Ethyl CorporationInventors: Kim R. Smith, Y.-D. Mark Chen, Rebecca F. Smith, James E. Borland, Joe D. Sauer
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Patent number: 5208374Abstract: A non-aromatic tert-amine is oxidized with hydrogen peroxide at about 20.degree.-100.degree. C. by a carbon dioxide-accelerated high solids process in which discoloration of the amine oxide product is minimized by diluting the carbon dioxide before allowing it to contact the reaction mixture so that the entire reaction is conducted in an atmosphere composed of carbon dioxide and an amount of inert gas, such as nitrogen or air, which is at least equal in volume to the amount of carbon dioxide.Type: GrantFiled: September 23, 1992Date of Patent: May 4, 1993Assignee: Ethyl CorporationInventors: James E. Borland, Fred J. Impastato, Kim R. Smith
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Patent number: 5164121Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a normally liquid polyethylene glycol as the sole organic solvent. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.Type: GrantFiled: August 26, 1991Date of Patent: November 17, 1992Assignee: Ethyl CorporationInventors: Kim R. Smith, James E. Borland, Joe D. Sauer
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Patent number: 5162408Abstract: N-Alkenyl substituted hydroxylamines of formula I ##STR1## where R.sub.1 and R.sub.2 are independently hydrogen, alkyl, aryl or phenylalkyl, and R.sub.3 to R.sub.7 are independently hydrogen, alkyl or substituted alkyl are very effective process stabilizers for polymeric systems providing melt flow stabilization and resistance to discoloration during processing at elevated temperatures as well as effective stabilizers for lubricant compositions.Type: GrantFiled: September 26, 1991Date of Patent: November 10, 1992Assignee: Ciba-Geigy CorporationInventors: Paul Odorisio, Joseph E. Babiarz
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Patent number: 5130488Abstract: Discrete tert-amine oxides, including non-hygroscopic tert-amine oxide dihydrates, are prepared by (A) reacting a concentrated aqueous hydrogen peroxide with a tert-amine corresponding to the formula RR'R"N in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; and R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons in a reaction mixture which is maintained stirrable throughout the reaction by the use, at least during the latter part of the reaction, of an organic solvent which solubilizes the reaction mixture at the reaction temperature but permits precipitation of the tert-amine oxide at a lower temperature and (B) adjusting the water content of the product, if necessary, to achieve a water/tert-amine oxide mol ratio not higher than about 2.1/1 before recovering the tert-amine oxide.Type: GrantFiled: October 1, 1990Date of Patent: July 14, 1992Assignee: Ethyl CorporationInventors: Kim R. Smith, James E. Borland
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Patent number: 5128348Abstract: Certain hexane and heptane amines including geometric and stereoisomers, agricultural compositions containing them and their use as fungicides.Type: GrantFiled: September 12, 1990Date of Patent: July 7, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gregory S. Basarab
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Patent number: 5087752Abstract: The subject invention relates to a method of synthesizing nitroxides from secondary amines. This method uses a suitable dioxirane compound such as dimethyldioxirane (DMD), which is relatively stable and simple to synthesize, as the oxidizing agent. A quantity of a secondary amine having no hydrogen atoms directly attached to the alpha carbon atoms is mixed with a 2x molar ratio of the dioxirane. In a first reaction, the secondary amine is oxidized to form a hydroxylamine; in a second reaction, the hydroxylamine is further oxidized to form a nitroxide. When the dioxirane loses an oxygen atom it converts into a ketone; for example, dimethyldioxirane is converted into acetone. This is very convenient, since the ketone byproduct is a solvent that can be easily removed after the reaction without causing interfering reactions. This method provides a simple, highly selective, rapid reaction with very high yields.Type: GrantFiled: September 12, 1990Date of Patent: February 11, 1992Assignee: Curators of the University of MissouriInventors: Robert W. Murray, Megh Singh
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Patent number: 5082940Abstract: Aromatic tertiary amines are oxidized by means of hydrogen peroxide in an inert solvent medium in the presence of a catalyst selected from metal selenium and compounds of selenium.The process is applied to the preparation of oxides of heterocyclic aromatic tertiary amines and oxides of non-heterocyclic tertiary amines, in which the nitrogen atom is substituted by at least 1 aromatic nucleus.Type: GrantFiled: September 5, 1990Date of Patent: January 21, 1992Assignee: Interox (Societe Anonyme)Inventors: Franz Legrand, Andre Lecloux, Paul Deschrijver
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Patent number: 5081300Abstract: N-substituted hydroxylamines of formula I ##STR1## where R.sub.1 and R.sub.2 are independently hydrogen, alkyl, alkenyl, aryl or phenylalkyl, and R.sub.3 to R.sub.7 are independently hydrogen, alkyl or substituted alkyl are very effective process stabilizers for polymeric systems providing melt flow stabilization and resistance to discoloration during processing at elevated temperatures as well as effective stabilizers for lubricant compositions.Type: GrantFiled: April 24, 1990Date of Patent: January 14, 1992Assignee: Ciba-Geigy CorporationInventors: Paul Odorisio, Joseph E. Babiarz
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Patent number: 5075501Abstract: Novel compounds which have particular utility in the preparation of dry formulations, such as laundry powders, are mixed tert-amine oxides wherein the molecules correspond to the formula RR'R"NO.multidot.nH.sub.2 O in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons; and n is 0, 1, or 2; at least some of the molecules being dihydrate molecules. The pure dihydrates are non-hygroscopic solids.Type: GrantFiled: October 1, 1990Date of Patent: December 24, 1991Assignee: Ethyl CorporationInventors: James E. Borland, Kim R. Smith
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Patent number: 5068430Abstract: Amine oxides, such as amine oxide dihydrates, which have become discolored by being prepared from tert-amines and hydrogen peroxide in a liquid medium constituting not more than 50% of the weight of the reaction mixture and in the presence of carbon dioxide are bleached by exposing them to visible light, preferably incandescent light having a luminosity of at least about 1750 lumens.Type: GrantFiled: July 26, 1990Date of Patent: November 26, 1991Assignee: Ethyl CorporationInventors: James E. Borland, Y.-D. Mark Chen, Joe D. Sauer, Kim R. Smith, Rebecca F. Smith
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Patent number: 5059625Abstract: The present invention relates to novel compounds represented by the formula: ##STR1## wherein R is an alkyl group having from about 8 to about 18 carbon atoms, and mixtures thereof, n has a value of from 1 to 6, R.sub.1 is selected from the group consisting of an alkyl group having from 1 to about 12 carbon atoms, or ##STR2## where the sum of n+m=2 to 12. These compounds possess antimicrobial activity and are useful as cleaning agents and preservatives, particularly in water-based functional fluids and surface coating compositions.Type: GrantFiled: October 1, 1990Date of Patent: October 22, 1991Assignee: Olin CorporationInventors: Michael Scardera, Frank R. Grosser
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Patent number: 5055614Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a nonionic surfactant as the sole organic solvent, at least a portion of the nonionic surfactant being a fatty alkanolamide corresponding to the formula ZC(O)NZ'Z" in which Z is an alkyl group containing 4-30 carbons, Z' is hydrogen or an alkyl or hydroxyalkyl group containing 1-3 carbons, and Z" is a hydroxyalkyl group containing 1-3 carbons. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.Type: GrantFiled: October 15, 1990Date of Patent: October 8, 1991Assignee: Ethyl CorporationInventors: Joe D. Sauer, Kim R. Smith, James E. Borland
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Patent number: 4820820Abstract: Cationic surface-active products of the formula:R.sub.1 --O[C.sub.2 H.sub.3 (R.sub.2)O--].sub.p [C.sub.2 H.sub.3 (CH.sub.2 OH)O].sub.(n-1) CH.sub.2 --CHOH--CH.sub.2 --Gin which R.sub.1 =C.sub.4 -C.sub.20 aliphatic radical, R.sub.2 =C.sub.4 -C.sub.20 alkyl, alkoxymethyl or alkenyloxy radical, p=1-2.5, n=2-20 and G denotes an amine or amine oxide group, and their salts are disclosed for use principally in cosmetics.Type: GrantFiled: September 23, 1987Date of Patent: April 11, 1989Assignee: L'OrealInventors: Henri Sebag, Guy Vanlerberghe
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Patent number: 4748275Abstract: A solid non-hygroscopic flakeable di-C.sub.14-30 alkyl C.sub.1-2 alkylamine oxide is made by reacting di-C.sub.14-30 alkyl C.sub.1-2 alkylamine with aqueous hydrogen peroxide containing at least 40 weight percent H.sub.2 O.sub.2 in the absence of a solvent.Type: GrantFiled: September 8, 1986Date of Patent: May 31, 1988Assignee: Ethyl CorporationInventors: Kim R. Smith, James E. Borland
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Patent number: 4661433Abstract: Aryl nitrones, of the type used in contrast enhancement photolithography techniques, are stabilized by adding thereto a drying agent such as molecular sieve, silica gel or an alkylalkoxysilane. The resulting compositions are substantially storage stable.Type: GrantFiled: December 31, 1984Date of Patent: April 28, 1987Assignee: General Electric CompanyInventor: Gary C. Davis
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Patent number: 4659565Abstract: Shampoo containing a di-C.sub.6-18 primary alkyl methylamine oxide hair conditioning agent, e.g. didecylmethylamine oxide, is very effective in improving hair body and flyaway control.Type: GrantFiled: July 1, 1985Date of Patent: April 21, 1987Assignee: Ethyl CorporationInventors: Kim R. Smith, Raymond O. Johannessen, James E. Borland
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Patent number: 4650904Abstract: A process for producing an aqueous solution of a straight-chain alkyl tertiary amine oxide and a branched-chain alkyl tertiary amine oxide by reacting aliphatic tertiary amines with an aqueous solution of hydrogen peroxide is disclosed. In this process, a tertiary amine which mainly consists of a branched-chain tertiary amine is first reacted with excess hydrogen peroxide, and then, a straight-chain alkyl tertiary amine which is substantially free of a branched-chain alkyl group is added to the reaction mixture for permitting further reaction with hydrogen peroxide. The process achieves a high overall conversion of the starting amines, and the final product has an extremely low level of residual hydrogen peroxide.Type: GrantFiled: November 30, 1984Date of Patent: March 17, 1987Assignee: Mitsubishi Petrochemical Company, LimitedInventor: Koichi Fujita
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Patent number: 4548744Abstract: Water-soluble ethoxylated amine oxides having clay soil removal/anti-redeposition properties are disclosed herein. These amine oxides are selected from ethoxylated monoamine oxides, ethoxylated diamine oxides, ethoxylated polyamine oxides, ethoxylated amine oxide polymers, and mixtures thereof. These amine oxides are useful at from about 0.05 to about 95% by weight in detergent compositions which further comprise from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant or mixture thereof. In addition to these detergent surfactants, the detergent composition can optionally comprise from 0 to about 80% by weight of a detergent builder.Type: GrantFiled: July 22, 1983Date of Patent: October 22, 1985Inventor: Daniel S. Connor
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Patent number: 4508651Abstract: The invention is directed to a process and intermediates for the preparation of 1.alpha.,25-dihydroxyergocalciferol as well as substantially pure and crystalline 1.alpha.,25-dihydroxyergocolciferol. The end-product 1.alpha.,25-dihydroxyergocalciferol is useful in the treatment of disease states which are characterized by insufficient amounts of 1.alpha.,25-dihydroxycholecalciferol.Type: GrantFiled: March 21, 1983Date of Patent: April 2, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Enrico G. Baggiolini, Andrew D. Batcho, Alfred Boris, Milan R. Uskokovic
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Patent number: 4492642Abstract: Lubricant and liquid fuel compositions containing a product made by reacting a borating agent with an ammoninated hydrocarbyl epoxide are provided. The invention also provides the product per se and a method of reducing fuel consumption in an internal combustion engine using fuel and lubricant compositions containing same.Type: GrantFiled: June 14, 1983Date of Patent: January 8, 1985Assignee: Mobil Oil CorporationInventor: Andrew G. Horodysky
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Patent number: 4425243Abstract: Foaming agents for use in oil and gas production comprising n-octyl dimethylamine oxide, n-decyl dimethylamine oxide, branched decyl dimethylamine oxide, and mixtures thereof, all of which generate copious quantities of stable foam even in the presence of brine and hydrocarbons.Type: GrantFiled: October 21, 1982Date of Patent: January 10, 1984Assignee: Millmaster Onyx Group, Inc.Inventors: Harold A. Green, Morris Weinstein, Kenneth W. Prodo
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Patent number: 4416808Abstract: Bis-betaine-amine oxides of the formula ##STR1## in which R is a saturated or an olefinically unsaturated hydrocarbon radical having 1 to 3 double bonds and 8 to 22 carbon atoms,n.sup.1 and n.sup.2 each is an integer of from 2 to 3, n.sup.1 and n.sup.2 optionally being identical or different,m.sup.1 and m.sup.2 each is an integer of from 1 to 4, m.sup.1 and m.sup.2 optionally being identical or different, anda, b, c and d, being identical or different, each is a number of from 1 to 5, with the proviso that the sum (a+b+c+d) is at most 10.The compounds are prepared from primary amines of the formula RNH.sub.2, by dicyanoalkylation, hydrogenation, ethoxylation, reaction with alkali metal salts of .omega.-halocarboxylic acids, and subsequent oxidation with hydrogen peroxide. They are surfactants of mild action and suitable for formulating cosmetic and industrial cleaning agents.Type: GrantFiled: November 8, 1982Date of Patent: November 22, 1983Assignee: Hoechst AktiengesellschaftInventors: Gunter Blaschke, Alwin Reng, Jochen M. Quack
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Patent number: 4415488Abstract: Triamine-trioxides of the formula ##STR1## in which R denotes a saturated or an olefinically unsaturated hydrocarbon radical which has 1 to 3 double bonds and 8 to 22 carbon atoms, n.sup.1 and n.sup.2 represent an integer from 2 to 3, and n.sup.1 and n.sup.2 can be identical or different, and a, b, c and d, which are identical or different, each is a number from 1 to 5, with the proviso that the sum (a+b+c+d) should be at most 10.The compounds are prepared from primary amines of the formula RNH.sub.2 by dicyanoalkylation, hydrogenation, ethoxylation and oxidation with hydrogen peroxide. They are suitable for formulating industrial and also cosmetic cleaning agents.Type: GrantFiled: November 8, 1982Date of Patent: November 15, 1983Assignee: Hoechst AktiengesellschaftInventors: Gunter Blaschke, Alwin Reng, Jochen M. Quack
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Patent number: 4399077Abstract: Perfluorinated surface-active block or random oligomers of the formula ##STR1## where R denotes a C.sub.2 -C.sub.18 -hydrocarbon or- hydrofluorocarbon radical,Y denotes a C.sub.6 -C.sub.13 -fluorocarbon or- hydrofluorocarbon radical which can contain a chain oxygen atom,Z denotes a group which confers solubility in water and p and q denote integers or decimal numbers from 0.5 to 30 are provided. They are suitable for use in cosmetic compositions for the treatment of hair. They slow down the flow of sebum and the rate at which hair becomes greasy again.Type: GrantFiled: June 4, 1980Date of Patent: August 16, 1983Assignee: L'OrealInventors: Guy Vanlerberghe, Henri Sebag
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Patent number: 4347381Abstract: The pink color content often produced in products such as amine salts, amine oxides, betaines, quaternary ammonium compounds or other compounds derived from long chain alkyl amines is eliminated by treating the products with trace amounts of a bleaching agent. Heating of the treated amine at relatively low temperatures for a short period of time enhances the effectiveness of the bleaching agent. Long chain alkyl amines having a pink color may be similarly treated.Type: GrantFiled: January 24, 1978Date of Patent: August 31, 1982Assignee: Ethyl CorporationInventor: Melvin E. Tuvell
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Patent number: 4307249Abstract: An improved process for preparing p-aminophenol by the catalytic hydrogenation of nitrobenzene in an aqueous acidic reaction medium containing a dimethylalkylamine oxide whereby the hydrogenation rate is increased and the selectivity of the reaction for p-aminophenol is improved.Type: GrantFiled: January 7, 1981Date of Patent: December 22, 1981Assignee: Mallinckrodt, Inc.Inventor: Edward L. Derrenbacker
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Patent number: 4275236Abstract: Disclosed are tertiary amine oxides which comprise an amine oxide nucleus substituted with an organic group and with two hydroxy groups which have carbon atoms in at least the .alpha., .beta. and .gamma. positions, a hydroxyl group on the .beta.-carbon atom, and have an effective chain length of at least 4 carbon atoms, said amine oxide being capable of being provided in ostensibly anhydrous form and being capable of being made at a concentration by weight of at least about 80% by oxidizing the corresponding tertiary amine with an oxidizing agent without solvent and without gelling during said oxidation.Type: GrantFiled: December 26, 1979Date of Patent: June 23, 1981Assignee: Sherex Chemical Company, Inc.Inventors: Gary W. Earl, Howard M. Hickman
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Patent number: 4263177Abstract: Disclosed is an amine oxide foam stabilizer for stabilizing a foam of an alkyl benzene sulfonate foaming agent, wherein said amine oxide foam stabilizer is represented by the following general structure: ##STR1## where, R.sub.1 is a C.sub.4 -C.sub.11 alkyl groupR.sub.2 is a C.sub.2 -C.sub.4 alkylene groupR.sub.3, R.sub.4 each, independently, is a C.sub.1 -C.sub.4 hydroxyalkyl group.Type: GrantFiled: June 27, 1979Date of Patent: April 21, 1981Assignee: Sherex Chemical Company, Inc.Inventors: Richard R. Egan, Michelle M. Watts