Processes Patents (Class 564/298)
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Patent number: 5578744Abstract: A catalytically active gel is described consisting of a silica matrix with uniform porosity, monomodal pore distribution and high surface area, within which one or metal oxides possessing catalytic activity are dispersed. A process for preparing this catalytic gel is also described.Type: GrantFiled: May 19, 1995Date of Patent: November 26, 1996Assignees: Eniricerche S.p.A., Snamprogetti S.p.A.Inventors: Angela Carati, Enrico Davini, Mario G. Clerici, Giuseppe Bellussi
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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: 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: 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: 5442113Abstract: 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: February 1, 1993Date of Patent: August 15, 1995Assignee: Albright & Wilson LimitedInventors: Michael Blezard, Glyn R. Jones, Moharam Ghadimi
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Patent number: 5399296Abstract: Disclosed are solid, concentrated, amine oxide surfactant compositions containing amine oxide- maleic acid salts. The molar ratio of maleic acid to amine oxide in such salts is about a 1:1. The salts are soluble in water at 25.degree. C. at a pH of above the pKa of the amine oxide. Also disclosed is a process for preparing such solid amine oxide surfactant compositions, which process comprises admixing maleic acid and amine oxide surfactants in at least about a 1:1 molar ratio, at a pH of at least about 1 units less than the pKa of the amine oxide, to thereby form a visible precipitate therein. The precipitate is separated from the mixture, preferably by mechanical means, and dried. The dried precipitate is a maleic acid-amine oxide salt which can be incorporated into cleaning products, especially solid or granular cleaning products, as a solid, concentrated source of amine oxide surfactant.Type: GrantFiled: April 22, 1994Date of Patent: March 21, 1995Assignee: The Procter & Gamble CompanyInventors: Thomas J. Wierenga, Raymond D. Young
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Patent number: 5389306Abstract: Disclosed is a process for making solid formulations containing amine oxide surfactants. Maleic acid, or a water soluble salt thereof, is admixed with an aqueous liquid amine oxide formulation, which formulation preferably contains from about 20% to about 40% by weight of an amine oxide surfactant. The molar ratio of maleic acid to amine oxide surfactant is at least about 1:1. Admixture pH is maintained at or below, or reduced to at least, about 1 unit below the pKa of the amine oxide to form a visible precipitate therein. The precipitate is separated from the mixture, preferably by mechanical means, and dried. The dried precipitate is a maleic acid-amine oxide salt which can be incorporated into cleaning products, especially solid or granular cleaning products, as a source of amine oxide surfactant.Type: GrantFiled: April 22, 1994Date of Patent: February 14, 1995Assignee: The Procter & Gamble CompanyInventors: Thomas J. Wierenga, Raymond D. Young
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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: 5324857Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from certain problems, especially in the presence of transition metals. These problems include both in situ generation of impurities and particularly nitrosamines, which are allegedly carcinogenic, and also impaired product formation. The problems can be ameliorated by employing in the reaction mixture free radical scavengers, including in particular phenols and polyhydroxy-substituted aromatic compounds. The scavengers are advantageously employed in conjunction with a metal chelating agent such as polycarboxylic acid or an organopolyphosphonic acid.Type: GrantFiled: April 28, 1992Date of Patent: June 28, 1994Assignee: Solvay InteroxInventor: Noel S. Shehad
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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: 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: 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: 5223644Abstract: Bicarbonates and/or carbonates are used in greater than catalytic amounts to inhibit the formation of nitrosamines during the preparation, storage and/or use of amine oxides.Type: GrantFiled: February 3, 1992Date of Patent: June 29, 1993Assignee: Albright & Wilson LimitedInventors: Michael Blezard, Glyn R. Jones
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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: 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: 5120469Abstract: 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 alcohol ethoxylate or other compound corresponding to the formula Z[OC(Z')HCH.sub.2 ].sub.m OH 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 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: May 17, 1990Date of Patent: June 9, 1992Assignee: Ethyl CorporationInventors: Kim R. Smith, James E. Borland, Joe D. Sauer
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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: 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: 5071594Abstract: A free-flowing granular heavy duty laundry detergent is made by blending with a detergent builder (e.g. Zeolite A) and optional other ingredients a discrete tert-amine oxide wherein the molecules correspond to the formual RR'R"NO.2H.sub.2 O 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.Type: GrantFiled: October 1, 1990Date of Patent: December 10, 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: 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: 5055232Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained be reacting a tertamine 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: May 18, 1990Date of Patent: October 8, 1991Assignee: Ethyl CorporationInventors: Joe D. Sauer, Kim R. Smith, James E. Borland
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Patent number: 5023376Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from the problems of in situ generation of nitrosamines, which are allegedly carcinogens, as impurities and impaired product formation, especially in the presence of transition metals.The problems can be ameliorated by employing a selected range of alkyleneaminopoly(methylenephosphonic acid) compounds such as cyclohexane-1,2-diaminotetra(methylenephosphonic acid).Type: GrantFiled: July 17, 1989Date of Patent: June 11, 1991Assignee: Interox AmericaInventors: Noel S. Shehad, Laurie L. Dussack, Dirk van Hemelrijk
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Patent number: 4970341Abstract: A process for accelerating the oxidation of tert-amines by hydrogen peroxide by conducting the reaction in the presence of an ascorbic acid promoter.Type: GrantFiled: February 24, 1987Date of Patent: November 13, 1990Assignee: Ethyl CorporationInventor: Teresa K. Summerford
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Patent number: 4970340Abstract: A highly concentrated aqueous solution of a di-C.sub.6-20 alkyl methylamine oxide containing at least 50 weight percent of the amine oxide can be made without gel formation by reacting at least 40 weight percent aqueous hydrogen peroxide with a di-C.sub.6-20 alkyl methyl or ethylamine. These concentrated solutions offer large freight savings in shipping the amine oxides to remote locations.Type: GrantFiled: January 23, 1986Date of Patent: November 13, 1990Assignee: Ethyl CorporationInventor: Kim R. Smith
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Patent number: 4960934Abstract: The reaction of aqueous hydrogen peroxide with tert-amines to yield tert-amine oxides is catalyzed by the addition of a promoter amount of ammonium carbonate, ammonium bicarbonate or ammonium carbamate or mixtures thereof.Type: GrantFiled: October 27, 1989Date of Patent: October 2, 1990Assignee: Ethyl CorporationInventors: Kim R. Smith, Joe D. Sauer
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Patent number: 4942260Abstract: Amine oxides which have low levels of nitrosamines or are substantially-free of nitrosamines are made by reacting tert-amines with hydrogen peroxide in the presence of carbon dioxide and aluminum metal.Type: GrantFiled: August 29, 1988Date of Patent: July 17, 1990Assignee: Ethyl CorporationInventors: Kathleen S. Laurenzo, Joe D. Sauer
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Patent number: 4889954Abstract: Tertiary amines are converted to amine oxides in high conversion and at a faster rate by including dialkylcarbonate in the reaction of the tert-amine with aqueous hydrogen peroxide. Ascorbic acid can be used as a co-catalyst.Type: GrantFiled: June 30, 1988Date of Patent: December 26, 1989Assignee: Ethyl CorporationInventors: Kathleen S. Laurenzo, Dennis P. Bauer
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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: 4588522Abstract: Betaine-amine oxides of the formula ##STR1## in which R denotes alkyl, alkenyl or hydroxyalkyl, each of which has 8-22 carbon atoms, R.sup.1 denotes hydrogen or methyl, R.sup.2 denotes ethylene, propylene or 2-hydroxypropylene, R.sup.3, R.sup.4 and R.sup.5 can be identical or different and denote C.sub.1 -C.sub.3 -alkyl or a group of the formula ##STR2## or R.sup.3 denotes a group of the formula --R.sup.2 --BR.sup.4 R.sup.5, X denotes a direct bond or a group of the formula--CO--,A and B denote a group of the formulae ##STR3## it being necessary for at least one amine oxide group and at least one betaine group to be present, a denotes 0 or 1, b denotes 1, 2 or 3, n denotes a number from 0 to 10 and m denotes 1, 2 or 3. These compounds are obtained by partially quaternizing the parent polyamines with the alkali metal salt of an .omega.-halogenocarboxylic acid and then oxidizing the non-quaternized nitrogen atoms. These betaine-amine oxides are suitable for use as surfactants in cleansing agents.Type: GrantFiled: April 13, 1983Date of Patent: May 13, 1986Assignee: Hoechst AktiengesellschaftInventors: Gunter Blaschke, Alwin Reng, Jochen M. Quack
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Patent number: 4565891Abstract: A process for the catalytic oxidation of nonaromatic tertiary amines to the respective amine oxides is disclosed. An aqueous solvent system containing the tertiary amine is formed with an initial pH about equal to or greater than the pKa of the tertiary amine. This aqueous system is contacted with gaseous molecular oxygen at an oxygen partial pressure of at least about 50 psi and a temperature of at least about 80.degree. C. in the presence of certain octacyanomolybdate or iron (III) salts. The resulting oxidation converts the tertiary amine to the respective amine oxide in good yield.Type: GrantFiled: July 19, 1984Date of Patent: January 21, 1986Assignee: The Procter & Gamble CompanyInventors: Paul E. Correa, Dennis P. Riley
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Patent number: 4504666Abstract: Disclosed is an improvement in process for oxidizing an aromatic amine to form an aromatic amine oxide wherein a reaction mixture of the aromatic amine and a peracid is formed and maintained under non-aqueous conditions at a temperature and for a time adequate until substantially all of the aromatic amine is formed into said aromatic amine oxide. The provision for eliminating water from the reaction mixture leads to near quantitative yields of aromatic amine oxide.Type: GrantFiled: June 4, 1982Date of Patent: March 12, 1985Assignee: Sherex Chemical Company, Inc.Inventors: Gary W. Earl, Howard M. Hickman
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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: 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: 4264776Abstract: Tertiary amines such as alkyl or benzyl amines are catalytically oxidized by oxygen over an activated carbon catalyst to selectively produce secondary amines.Type: GrantFiled: January 2, 1976Date of Patent: April 28, 1981Assignee: Monsanto CompanyInventors: Arnold Hershman, Donald J. Bauer
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Patent number: 4247480Abstract: An amine oxide is produced by oxidizing a tertiary amine having the formula ##STR1## wherein R.sub.1 and R.sub.2 respectively represent methyl or ethyl group; and R.sub.3 represent a C.sub.8 -C.sub.14 alkyl or alkenyl group in the presence of carbon dioxide and in the presence or absence of an improver selected from the group consisting of ethylenediaminetetraacetic acid, its salts, stanates, polyphosphates, salts of hydroxycaboxylic acid and salts of polycarboxylic acid.Type: GrantFiled: August 9, 1979Date of Patent: January 27, 1981Assignee: Nissan Chemical Industries LimitedInventors: Atsuo Murata, Syuji Tsuchiya, Akihiro Konno, Fumiyoshi Arima, Hisao Ikeda