Hydroxy, Bonded Directly To Carbon, Or Ether Containing (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/292)
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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: 5196418Abstract: Compounds of the present invention are those having the formula: ##STR1## where R is a linear or branched chain of 1 to 22 carbon atoms selected from the group consisting of alkyl, alkenyl or alkynyl or said C.sub.1 to C.sub.22 chains substituted with --SR.sub.3, --OR.sub.3, --NHR.sub.3, --CH.sub.3, or --C(O)OR.sub.2 where R.sub.2 is hydrogen or C.sub.1 to C.sub.6 alkyl; R.sub.1 is hydrogen, C.sub.1 to C.sub.6 alkyl, --SR.sub.3, --OR.sub.3, --NHR.sub.3, --NR'.sub.3 R.sub.3, or --C(O)OR.sub.2 where R.sub.2 is as previously defined; R.sub.3 and R'.sub.3 are the same or different and are hydrogen, C.sub.1 to C.sub.6 alkyl, alkylthioalkyl, alkoxyalkyl, aminoalkyl, aminoalkyl substituted with phenyl, substituted phenyl, benzoyl, substituted benzoyl, heteroaryl or substituted heteroaryl; R.sub.4 is hydrogen, C.sub.1 to C.sub.6 alkyl, or --C(O)OR.sub.2 where R.sub.2 is defined previously; R.sub.5 is hydrogen, C.sub.1 to C.sub.6 alkyl, phenyl, or substituted phenyl; R.sub.6 is hydrogen, C.sub.1 to C.sub.Type: GrantFiled: February 14, 1992Date of Patent: March 23, 1993Assignee: Board of Supervisors, Louisiana State University Agricultural & Mechanical CollegeInventors: Richard D. Gandour, Gnanasambandam Kumaravel
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Patent number: 5196582Abstract: Quaternary ammonium halides are prepared in solid form by reacting an alkyl or aralkyl halide with ammonia or an amine in a liquefied gas as the solvent.Type: GrantFiled: July 1, 1991Date of Patent: March 23, 1993Assignee: Ethyl CorporationInventors: Kim R. Smith, James E. Borland, Jeffrey W. Perine, Joe D. Sauer
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Patent number: 5171641Abstract: An acid copolymer/quaternary amine mixture is disclosed which is permanently antistatic. The acid copolymer is a copolymer of (i) a major amount by mol % of an alpha-olefin of the formula RCH.dbd.CH.sub.2 wherein R is H or C.sub.1 to C.sub.8 alkyl, and (ii) a minor amount by mol % of an alpha,beta-ethylenically unsaturated carboxylic acid. The quaternary amine is of the formula [(R.sup.1)(R.sup.2)(R.sup.3)(R.sup.4)N].sup.+ [X].sup.- wherein R.sup.1 is selected from H, aryl, or C.sub.1 to C.sub.50 alkyl optionally having one or more non-contiguous C.dbd.O or NHC.dbd.O or --S-- or --O-- in the carbon chain, or the same as R.sup.2 ; each of R.sup.2, R.sup.3, and R.sup.4 is the same or different and selected from H, C.sub.1 to C.sub.18 alkyl optionally substituted with one or more OH or from --(R.sup.5 --O).sub.a --H where a is an integer from 1 to 10 and R.sup.5 is ethylene or propylene; and X is an anion selected from chloride, bromide, iodide, nitrate, fluoborate, phosphate, C.sub.1 to C.sub.Type: GrantFiled: July 25, 1990Date of Patent: December 15, 1992Assignee: W. R. Grace & Co.-Conn.Inventors: William P. Roberts, Marvin R. Havens
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Patent number: 5162048Abstract: The present invention relates to an additive to hydrocarbon fuels which includes nitrate of ethanolamine as an additive to reduce the quantity of smoke and improve the efficiency of combustion. The invention also relates to a process for the preparation of this additive and of the fuels improved by the addition of the additive.Type: GrantFiled: August 20, 1990Date of Patent: November 10, 1992Assignee: Kirsten, Inc.Inventor: Samuel Diaz-Valdes
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Patent number: 5152916Abstract: Aqueous aldehyde solutions for trapping hydrogen sulfide comprising 5 to 50% by weight of an aldehyde and 1 to 5% by weight, relative to the aldehyde solution of a formulation comprising10 to 80% by weight of an ester of oxalkylated alkylalkylenediamines, which may be quaternized and 20 to 90% by weight of water or of a C.sub.1 -C.sub.4 -alcohol.Type: GrantFiled: August 21, 1990Date of Patent: October 6, 1992Assignee: Hoechst AktiengesellschaftInventors: Hermann Hoffmann, Frederic Mabire
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Patent number: 5147411Abstract: Process for improving the color yield and the wet fastness properties of dyeings or prints produced with anionic dyes on cellulose fibre material, in which the fibre material is treated before dyeing or during a dyeing with a quaternary ammonium salt of the formula ##STR1## in which R is C.sub.1 -C.sub.3 alkyl, X is the group ##STR2## Hal is a halogen atom and Q.sup..crclbar. is the anion of an aromatic sulfonic acid or a C.sub.1 -C.sub.3 alkylsulfate ion.Type: GrantFiled: March 11, 1991Date of Patent: September 15, 1992Assignee: Ciba-Geigy CorporationInventor: Rosemarie Topfl
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Patent number: 5137919Abstract: The invention relates to a novel compound, compositions and medicaments thereof and a method of inhibiting cell proliferation, platelet aggregation (induced by various factors), and inhibiting malignant phenotypes of tumor cells such as those having a metastatic property, using said compound, composition or medicament. N,N,N-trimethylsphingosine shows superior cell proliferation inhibitory and anti-metastatic activity over related compounds.Type: GrantFiled: December 31, 1990Date of Patent: August 11, 1992Assignee: Biomembrane InstituteInventors: Yasuyuki Igarashi, Mahammad N. Ahmad, Hirofumi Okoshi, Sen-Itiroh Hakomori
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Patent number: 5136095Abstract: Compounds and methods are disclosed for reversibly aggregating particles suspended in a liquid medium. The method comprises combining the liquid medium containing the particles with a polyionic polymer capable of aggregating the particles under conditions suitable for such aggregation. Thereafter, the particles are contacted with a chemical reagent capable of cleaving the polyionic polymer under conditions sufficient to reverse the aggregation. Optionally, magnetic particles are added to the liquid medium in the present method under conditions for non-specific binding and the medium including the aggregates is subjected to a magnetic field gradient to separate the aggregates from the medium. The compounds of the present invention are polyions. The aggregation of the particles is reversible upon contact with chemical agents which cleave at least some of the bonds within the polyionic polymer.Type: GrantFiled: December 1, 1988Date of Patent: August 4, 1992Assignee: Syntex (U.S.A.) Inc.Inventors: Thomas L. Tarnowski, Cheng-I Lin, Edwin F. Ullman
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Patent number: 5077435Abstract: The present invention is a process for producing halohydroxypropyltrialkylammonium halides by reacting a trialkylamine salt with an epihalohydrin, the improvement comprising using 1,3-dihalo-2-propanol as a cosolvent. Using that cosolvent reduces the amount of diquaternary, dichloropropanol, and epoxy by-products formed. The cosolvent is preferably separated from the reaction mixture and recycled for use with additional trialkylamine salt and epihalohydrin. The process is particularly useful in preparing chlorohydroxypropyltrimethylammonium chloride.Type: GrantFiled: September 12, 1990Date of Patent: December 31, 1991Assignee: The Dow Chemical CompanyInventors: Russell B. Kimbrell, Christian D. Kneupper, Ruben L. Krause
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Patent number: 5075165Abstract: A composite paint film formed on a steel sheet of an automotive vehicle body. The composite paint film comprises an electrodeposition paint film (I) coated on the steel sheet, and an intermediate coat paint film (II) coated on the first paint film. The electrodeposition paint film is formed of an epoxy-based cationic electrodeposition paint composition and has a minimum melt viscosity not less than 0.2 during hardening. The epoxy-based cationic electrodeposition paint composition includes an amine-added epoxy resin (1) of the type which may be hardened with a blocked isocyanate, a colloidal silica-containing gelled particulate (2), and an alkyltin ester compound of a liquid aliphatic carboxylic acid. The above-mentioned colloidal silica-containing gelled particulate is formed by dispersing a mixture of an acrylic copolymer having a hydrolizable alkoxysilane group and a cationic group and a cationic acidic colloidal silica in water to carry out a cross-linking reaction in particles of the colloidal silica.Type: GrantFiled: May 11, 1990Date of Patent: December 24, 1991Assignee: Nissan Motor Company, Ltd.Inventors: Hiroyuki Kishi, Hitoshi Kimura, Katsuya Yamamoto, Yoshinobu Tamura, Tsuneo Sakauchi, Masahide Nagaoka, Yoichi Masubuchi, Eisaku Nakatani
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Patent number: 5068431Abstract: Aliphatic surface active compounds containing a propylene chain bonded at one end to a cationic quaternary ammonium group and at the other end to an amphoteric amine oxide group, and methods of making and using them.Type: GrantFiled: May 15, 1989Date of Patent: November 26, 1991Assignee: Witco CorporationInventors: Anastasios Karalis, Thomas Morong, Charles Juszkiewicz
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Patent number: 5053531Abstract: Described are certain quaternary ammonium alkyl benzene sulfonate salts and certain quaternary ammonium alkane sulfonate salts, e.g., octyl dimethyl hydroxyethyl ammonium dodecyl benzene sulfonate and octyl dimethyl hydroxyethyl ammonium methane sulfonate which are useful as antistatic agents for synthetic polymer articles.Type: GrantFiled: December 12, 1989Date of Patent: October 1, 1991Assignee: PPG Industries, Inc.Inventor: Cheruthur Govindan
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Patent number: 5015754Abstract: Quaternized condensation products useful as aftertreating agents for fixing reactive dyeings and prints on textile materials which contain cellulose fibers are formed fromA) a precondensate of one or more trialkanolamines I ##STR1## (R.sup.1 -R.sup.3 =C.sub.2 -C.sub.4 -1,2-alkylene), B) a) a carboxylic acid or a derivative thereof IIa ##STR2## [n=0, 1; R.sup.4, R.sup.5 =OH (except if n=0), C.sub.1 -C.sub.8 -alkoxy (possibly joined together to form a 5- or 6-membered ring if n=0), Cl, Br; R.sup.6 =C.sub.1 -C.sub.50 -alkylene (possibly interrupted by one or more nonadjacent oxygen atoms)],b) a carboxamide IIb ##STR3## [m, n, r=0, 1; R.sup.7 =H, C.sub.1 -C.sub.4 -alkyl; R.sup.8 =H, C.sub.1 -C.sub.25 -alkyl, C.sub.2 -C.sub.25 -alkenyl, Ph (possibly substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, F, Cl, Br)],c) an epihalohydrin IIc, ##STR4## d) a monofunctional compound IIdR.sup.9 --Y IId[R.sup.9 =C.sub.1 -C.sub.25 -alkyl, C.sub.2 -C.sub.25 -alkenyl, Ph (possibly substituted by C.sub.1 -C.sub.Type: GrantFiled: August 21, 1989Date of Patent: May 14, 1991Assignee: BASF AktiengesellschaftInventors: Johannes P. Dix, Rolf Fikentscher, Ingrid Steenken-Richter
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Patent number: 4997912Abstract: Fatty acid esters of oxalkylated alkylalkylenediamines, which may be quaternized:Esters of oxalkylated alkylalkylenediamines, which may be quaternized, of the formula ##STR1## where the individual symbols have the meaning given in the description, process for their production and their use as corrosion inhibitors, particularly in crude oil recovery plants and crude oil treatment plants.Type: GrantFiled: December 15, 1988Date of Patent: March 5, 1991Assignee: Hoechst AktiengesellschaftInventors: Herbert Wirtz, Hermann Hoffmann, Werner Ritschel, Manfred Hofinger, Michael Mitzlaff, Dietrich Wolter
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Patent number: 4992211Abstract: The invention relates to novel alkylene oxide-containing amphoteric compounds and to their use as surface active agents. The novel amphoteric compounds are especially useful in the cosmetics and toiletries areas, e.g., as surfactants in shampoo compositions.Type: GrantFiled: November 21, 1989Date of Patent: February 12, 1991Assignee: Sandoz Ltd.Inventor: Robert V. Casciani
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Patent number: 4983748Abstract: Polysaccharide aldehydes having the formula Sacch--O--CH.sub.2 --CH.dbd.CH--CHO, Saach--O--CH.sub.2 --C.tbd.C--CHO, ##STR1## starch, cellulose, and gum aldehydes, are useful for imparting wet, dry, or temporary wet strength to paper. They are prepared by a non-oxidative method which involves reacting the polysaccharide base, in the presence of alkali, with a derivatizing acetal reagent having the general structure ##STR2## and then hydrolyzing the acetal by adjusting the pH to less than 7, preferably 2-4. In the formulas, n is 1-3; R.sup.11 and R.sup.12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R.sup.11 or R.sup.12 is one of the groups when n is 2, or R.sup.11 and R.sup.12 are not present when n is 3; R.sup.13 is an alkyl group, optionally containing an ether linkage, or an aralkyl group; R.sup.14 and R.sup.15 are individually a hydrogen or a methyl group; R.sup.16, R.sup.17, and R.sup.18 are individually an alkyl group; Y.sup.Type: GrantFiled: December 28, 1988Date of Patent: January 8, 1991Assignee: National Starch and Chemical Investment Holding CorporationInventors: John J. Tsai, Patrick G. Jobe, Diane J. Lamb, Robert L. Billmrs, Martin M. Tessler
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Patent number: 4982000Abstract: The present invention is directed to a process for preparing a quaternary ammonium compound which comprises the reaction product of (a) a tertiary amine; (b) an alkylating agent characterized by the presence of a first member selected from the group consisting of hydroxyl and thiol radicals and a second member, a halogen atom, disposed on adjacent carbon atoms; and (c) an epoxy compound acting as an entraining reactant.Type: GrantFiled: November 3, 1989Date of Patent: January 1, 1991Assignee: Sherex Chemical Co., Inc.Inventors: Gary W. Earl, Owen Portwood
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Patent number: 4883917Abstract: Disclosed herein are quaternary ammonium compounds of the formula R.sup.1 R.sup.2 R.sup.3 N.sup.+ --(CH.sub.2).sub.m Y X.sub.n.sup.- wherein n is 1 or 2 depending on the valence of the cation; m is an integer from 1 to 6; Y is a group selected from Z, --N.sup.+ R.sup.1 R.sup.2 R.sup.3, --OH, --SOCl, --CH.tbd.CH.sub.2, --O--R.sup.4, --OSiR.sup.5 R.sup.6 R.sup.7, --OC(O)R.sup.8, --CN, --SO.sub.4 Q, --C.dbd.CH, epoxide, --SR.sup.10, --S(O.sub.2)R.sup.11, --S(O)R.sup.12, ##STR1## SO.sub.3 Q, --Si(OR.sup.13)(OR.sup.14)-- (OR.sup.15), --OC(O)--(CH.sub.2).sub.p --C(O)--O--(CH.sub.2).sub.m --NR.sup.1 R.sup.2 R.sup.3, and --NR.sup.16 R.sup.17 wherein m and p are integers, the R groups are hydrocarbyl, Q is H or alkali metal. They are useful as fungicides, herbicides, antiseptics and peroxygen bleach activators.Type: GrantFiled: October 1, 1985Date of Patent: November 28, 1989Assignee: Ethyl CorporationInventors: Kim R. Smith, Joe D. Sauer, James E. Borland
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Patent number: 4880894Abstract: Novel quaternary ammonium salts of general formula (I) ##STR1## wherein: R is a saturated or unsaturated, linear or branched alkyl radical of C.sub.1 to C.sub.8.R' is a saturated or unsaturated, linear or branched alkyl radical of C.sub.1 to C.sub.12, or a benzyl radical.n is a number equal to 2 or 3.X.sup..theta. is a halogenide anion, such as Cl.sup..theta., Br.sup..theta., I.sup..theta., are used as phase transfer catalysts, in heterogeneous ionic reactions wherein the reagents are in different phase and have different polarity.Type: GrantFiled: September 26, 1988Date of Patent: November 14, 1989Assignee: Alter, S.A.Inventors: Carlos Sunkel, Miguel Fay de Casa Juana, Fernando Dorrego, Basilio Pando, Julio Alvarez-Builla, Juan J. Vaquero, Carlos Galera, Maria L. Vazquez
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Patent number: 4864060Abstract: Aliphatic surface active compounds containing a propylene chain bonded at one end to a cationic quaternary ammonium group and at the other end to an amphoteric amine oxide group, and methods of making and using them.Type: GrantFiled: August 31, 1987Date of Patent: September 5, 1989Assignee: Witco CorporationInventors: Anastasios Karalis, Thomas Morong, Charles Juszkiewicz
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Patent number: 4845289Abstract: A process for the removal or reduction of residual trimethyl amine odor resulting from the quaternization of a halogen containing precursor with trimethyl amine. Odor reduction is achieved by reacting the residual trimethyl amine with at least an equivalent amount of methyl chloride at a temperature of at least 50.degree. C. for a period of time to convert substantially all of the trimethyl amine to tetramethyl ammonium chloride.Type: GrantFiled: February 29, 1988Date of Patent: July 4, 1989Assignee: Nalco Chemical CompanyInventors: Donald G. Ries, Allan W. Smith
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Patent number: 4843176Abstract: This invention relates to the following:(1) An amino-containing composition characterized by polymercapto groups,(2) A polyamino-containing composition characterized by mercapto or polymercapto groups,(3) A composition characterized by the presence ofA. a mercapto or polymercapto groups, andB. a nitrogen-containing group characterized by at least one of the following:1. an amido or a polyamido group,2. a cyclic amidine or a polycyclic amidine group,3. an epihalohydrin-derived amino-containing group.This invention also relates to the use of the above compositions as corrosion inhibitors.Type: GrantFiled: October 25, 1985Date of Patent: June 27, 1989Assignee: Petrolite CorporationInventors: Neil E. S. Thompson, Derek Redmore, Bernardus A. Oude Alink, Benjamin T. Outlaw
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Patent number: 4836958Abstract: The instant invention relates to fluorinated cationic compounds of the formula ##STR1## wherein R.sub.f is a perfluoroalkyl or perfluoroalkoxy-perfluoroalkyl group;R.sub.1 is alkylene optionally interrupted by --O--, --S--, --SO.sub.2 --, --SO.sub.2 NR'--, --CO.sub.2 --, --NR'--, or --CONR'-- where R' is hydrogen or lower alkyl;m is 0, 1 or 2;R.sub.2 is linear or branched alkylene;R.sub.3, R.sub.4, and R.sub.5 independently of one another represent alkyl or arylalkyl groups which are unsubstituted or substituted by hydroxyl, lower alkoxy, halogen, cyano or by polyalkyleneoxy, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical or R.sub.3, R.sub.4 and R.sub.5 together with nitrogen atom that links them represent a substituted or unsubstituted pyridine ring; andA.sup..crclbar. represents the anion of an organic or inorganic acid; and their particular use as surfactants.Type: GrantFiled: July 31, 1986Date of Patent: June 6, 1989Assignee: Ciba-Geigy CorporationInventor: Athanasios Karydas
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Patent number: 4824602Abstract: The present invention relates to processes for purifying quaternary cationic surfactant materials and rendering said materials substantially free of ultraviolet absorbing impurities having a maximum absorption in the range of from about 260 nm to about 280 nm. This invention also relates compositions containing purified quaternary cationic surfactant materials.Type: GrantFiled: December 22, 1987Date of Patent: April 25, 1989Assignee: The Procter & Gamble CompanyInventor: Prem S. Juneja
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Patent number: 4814506Abstract: A process for preparing 3-halogeno-2-hydroxy-propyltrimethylammonium halide or especially one having the (S)-configuration, which comprises reacting 2,3-dihydroxypropyltrimethylammonium halide or one having the (S)-configuration, which is obtained by reacting (R)-3-halogeno-1,2-propanediol with trimethylamine, with a halogenating reagent.According to the present invention, 3-halogeno-2-hydroxypropyltrimethylammonium halide or one having the (S)-configuration, which is a useful intermediate for the synthesis of carnitine or especially (l)-carnitine, can be obtained economically, efficiently and easily.Type: GrantFiled: August 21, 1987Date of Patent: March 21, 1989Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Kazuhiko Katayama, Shigeki Hamaguchi, Yoshikazu Kogame, Takehisa Ohashi, Kiyoshi Watanabe
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Patent number: 4812263Abstract: Described are bis-quaternary ammonium compounds of 2-hydroxypropylene, e.g., 2-hydroxy propylene-1,3-bis(dimethyl stearyl ammonium chloride).Type: GrantFiled: March 28, 1988Date of Patent: March 14, 1989Assignee: PPG Industries, Inc.Inventor: Robert B. Login
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Patent number: 4778813Abstract: Novel capped polymeric quaternary ammonium compositions formed by reacting ionene type polymers with tertiary amines are useful as microbicides, corrosion inhibitors, debonding agents, flocculants, softeners, and demulsifiers.Type: GrantFiled: January 30, 1985Date of Patent: October 18, 1988Assignee: Buckman Laboratories International, Inc.Inventors: Joseph G. Fenyes, John D. Pera
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Patent number: 4764306Abstract: A method of preparing certain bis-quaternary ammonium compounds and mixtures is disclosed. The method involves contacting a tertiary amine with a suitable amount of neutralizing acid, e.g. HCl, and subsequently contacting the resulting mixture with a suitable epoxide, e.g. epichlorohydrin, at an elevated temperature and in an amount that e.g. 2-hydroypropylene-bis-1,3-(dimethyl stearyl ammonium chloride) is obtained in almost stoichiometric yields. The resulting bis-quaternary ammonium compounds can be incorporated into a hair conditioner whereby a softer feel and better control of hair is obtained.The general structure for the resulting bis-quaternary ammonium compounds is as follows: ##STR1## wherein the R's are selected from the group consisting of alkyl, alkylamidoalkyl, aryalkyl, aryl, alkoxy, alkenyl, hydroxyalkyl, and carboxyalkyl and X is a negative radical from the epoxide used, e.g. epichlorohydrin.Type: GrantFiled: August 22, 1986Date of Patent: August 16, 1988Assignee: PPG Industries, Inc.Inventor: Robert B. Login
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Patent number: 4722978Abstract: A cationic ring-opening polymerization of a cyclic ether ("CE") in conjunction with an unsaturated alcohol (propagator) having an allyl double bond, produces a polyether macromer having an allylic group near one end and a hydroxyl group at the other. The polymerization proceeds by polyaddition of the CE to the OH group which is the propagating species. The CE is an alkylene oxide or an aliphatic or aromatic glycidyl ether; the propagator is a primary or secondary alcohol which, if cyclic may have a single internal double bond in one ring. The catalyst is a Friedel-Crafts acid, strong protic organic or inorganic acid, oxonium salt, or the like.Type: GrantFiled: August 30, 1985Date of Patent: February 2, 1988Assignee: The B. F. Goodrich CompanyInventor: Simon H. Yu
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Patent number: 4709083Abstract: A method of synthesizing boron analogues of choline and choline related mrials is disclosed. The method comprises reacting N,N dimethylethanolamine with hydrogen chloride or an acid chloride to form an ester hydrochloride. The resulting aminoalcohol hydrochloride or ester hydrochloride is further reacted with tetraethyl NBH.sub.4.Also disclosed are pharamaceutically interesting compounds of acetylcholine.Type: GrantFiled: May 19, 1986Date of Patent: November 24, 1987Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Bernard F. Spielvogel
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Patent number: 4692543Abstract: Process for the production of optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-oxy-propyltrimethylammonium-chloride is converted by racemate resolution with CaCl.sub.2, for example, into the optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated into calcium tartrate and optically-active 3-chloro-2-oxy-propyltrimethylammonium-chloride, and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.Type: GrantFiled: February 25, 1986Date of Patent: September 8, 1987Assignee: Lonza Ltd.Inventors: Leander Tenud, Jacques Gosteli
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Patent number: 4675180Abstract: Compounds of the formula ##STR1## in which R.sub.1 is long-chain alkyl, R.sub.2 and R.sub.3 are each lower alkyl and X.crclbar. is an anion, are prepared by quaternizing amines of the formula R.sub.1 R.sub.2 R.sub.3 N with ethylene oxide in the presence of acid. This gives the quaternary compounds in virtually quantitative yield. The compounds are particularly suitable for use in hair cosmetics.Type: GrantFiled: February 18, 1986Date of Patent: June 23, 1987Assignee: Ciba-Geigy CorporationInventor: Franz Gunter
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Patent number: 4661634Abstract: Particles, fibers, or filaments of alkali salts of ethylene/carboxylic acid copolymers or terpolymers, especially in highly porous form, are employed in removing contaminants from tertiary amines or quaternary amine salts, especially metal contaminants.Type: GrantFiled: September 16, 1985Date of Patent: April 28, 1987Assignee: The Dow Chemical CompanyInventors: Walter L. Vaughn, Milton S. Wing
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Patent number: 4638089Abstract: A fluorine-containing quaternary ammonium compound of the formula: ##STR1## wherein R.sub.f is a fluorine-containing straight or branched aliphatic hydrocarbon or polyether group, R.sub.1, R.sub.2 and R.sub.3 are each a C.sub.1 -C.sub.21 straight or branched alkyl, hydroxyalkyl or alkenyl group or a substituted or unsubstituted aryl or aralkyl group, R.sub.4 is a hydrogen atom or a acyl group, X.sup.- is an anion and n is an integer of 1 to 3, having a capability of reducing the surface tension of water and the interfacial tension between water and oil.Type: GrantFiled: April 24, 1981Date of Patent: January 20, 1987Assignee: Daikin Kogyo Co., Ltd.Inventors: Iwao Hisamoto, Chiaki Maeda, Mitsuhiro Nishiwaki
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Patent number: 4602110Abstract: A method of purifying 3-chloro-2-hydroxypropyl trialkylammonium chloride. An aqueous slurry is prepared containing about 70-98 wt. % total solids including the chloride and impurities associated with the preparation thereof. To this slurry is then added a miscible alcohol having about 3-4 carbon atoms. A solid filtrate is collected and optionally washed with additional alcohol and dried. The solid filtrate is substantially more pure in the chloride than the starting material.Type: GrantFiled: May 15, 1985Date of Patent: July 22, 1986Assignee: The Dow Chemical CompanyInventor: Emmett L. Tasset
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Patent number: 4594452Abstract: The preparation of anhydrous, pure, crystalline N-(3-chloro-2-hydroxypropyl) trialkylammonium salts is disclosed by a process entailing reaction of epichlorohydrin with a trimethylammonium salt in an organic solvent which is a solvent for the two reactants and a non-solvent for the reaction product.A fine crystalline, chemically pure, anhydrous N-(3-chloro-2-hydroxypropyl) trimethylamine hydrochloride is produced by a process that does not entail an aqueous medium or the use of gaseous trimethylamine. The process comprises reacting trimethylammonium chloride with epichlorohydrin in an organic solvent which is a solvent for either of the two reactants and a non-solvent for the reaction product. Though a number of organic solvents may be used, it was found that chloroform was particularly suited. The reaction proceeds readily at temperatures within the range of 0.degree. to 50.degree. C.Type: GrantFiled: June 24, 1985Date of Patent: June 10, 1986Assignee: Allied CorporationInventors: Herbert K. Reimschuessel, Michael A. Kocur
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Patent number: 4540521Abstract: This invention relates to improved liquid quaternary ammonium compositions obtained by quaternizing a mixture of amines with essentially a stoichiometric amount of a di(C.sub.1-4 alkyl)sulfate, said amine mixture containing 80 to 99.5 weight percent of an alkoxylated ether amine of the formula ##STR1## where R is an aliphatic hydrocarbon radical having from 2 to 20 carbon atoms, R' is hydrogen or methyl and x and y are integers from 1 to 20, and 0.5 to 20 weight percent of a trialkanolamine of the formula ##STR2## where z is an integer from 1 to 6. The quaternary ammonium compositions are useful as antistatic agents for a variety of synthetic fibers, yarns and fabrics.Type: GrantFiled: January 16, 1984Date of Patent: September 10, 1985Assignee: National Distillers and Chemical CorporationInventors: Roger H. Garst, Frank N. Tuller, Charles R. Tucker
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Patent number: 4540725Abstract: A quaternary ammonium group-containing material which is obtained from reacting a polyepoxide with an amine containing at least one acyclic group of about 8 to 30 carbon atoms and optionally an amine containing an alkylarylpoly ether moiety is disclosed. The resins are useful as pigment grinding vehicles and in the formulation of pigment paste, particularly pigment paste with high pigment loadings. When formulated into cationic electrodepositable compositions, the pigment grinding vehicles provide for cured electrodeposited coatings of excellent corrosion resistance, particularly over untreated and oily steel.Type: GrantFiled: August 15, 1984Date of Patent: September 10, 1985Assignee: PPG Industries, Inc.Inventors: Robert D. Jerabek, Jeffrey G. Koren, Mark W. Johnson
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Patent number: 4505839Abstract: Polyalkanolamines of controlled molecular weights and their uses as demulsifiers and/or flotation agents.Type: GrantFiled: May 18, 1981Date of Patent: March 19, 1985Assignee: Petrolite CorporationInventors: Thomas J. Bellos, Eva G. Lovett
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Patent number: 4492802Abstract: Process for the manufacture of quaternary ammonium compounds by reacting a compound having a terminal epoxide troup with a salt of a tertiary amine in the presence of a quaternary ammonium compound as catalyst.Type: GrantFiled: April 19, 1982Date of Patent: January 8, 1985Assignees: Henkel Kommanditgesellschaft auf Aktien, Degussa AktiengesellschaftInventors: Horst Rutzen, Peter Nikolaus, Martin Bischoff, Rudolf Lehmann
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Patent number: 4485259Abstract: A novel quaternary ammonium group-containing material which is obtained from reacting a monoepoxide with an amine containing at least one organic group containing an acyclic moiety of from about 8 to 30 carbon atoms is disclosed. The quaternary ammonium group-containing materials are useful as pigment grinding vehicles and in the formulation of pigment paste, particularly pigment paste with high pigment loadings. When formulated in cationic electrodepositable compositions, the pigment grinding vehicles provide for cured electrodeposited coatings of excellent corrosion resistance, particularly over untreated and oily steel.Type: GrantFiled: September 30, 1982Date of Patent: November 27, 1984Assignee: PPG Industries, Inc.Inventors: Robert D. Jerabek, Jeffrey G. Koren, Mark W. Johnson
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Patent number: 4482713Abstract: Novel quaternary ammonium salts of the general formula[R.sup.1 R.sup.2 R.sup.3 N(A--O).sub.n --R.sup.4 ].sup.+ Z.sup.-where R.sup.1 and R.sup.2 are identical or different and each is alkyl, aryl, aralkyl, alkylaryl, alkoxyalkyl, or a (poly)alkylene glycol radical, or R.sup.1 and R.sup.2, together with the nitrogen atom, are a heterocyclic ring, or one or more substituents R.sup.1 or R.sup.2 are polyfunctional so that the salt contains not less than 2 ammonium groups, R.sup.3 and R.sup.4 are identical or different monovalent radicals of one or more alkylating agents R.sup.3 X or R.sup.4 X, for example an (ar)alk(en)yl halide, sulfate or methosulfate or an (alkyl)aryl-sulfonate or -sulfonic acid ester, A is alkylene of 2 to 10 carbon atoms, n is an integer and Z is either X or another salt-forming anion or a hydroxyl ion, are prepared by N-alkylation and O-alkylation of an alkanolamine with the aid of a phase transfer catalyst and are useful as cationic surfactants, etc.Type: GrantFiled: July 1, 1982Date of Patent: November 13, 1984Assignee: BASF AktiengesellschaftInventor: Rainer Strickler
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Patent number: 4480126Abstract: Process for the preparation of quaternary ammonium compounds by reacting a tertiary amine with a vicinal halohydrin having at least 6 carbon atoms, and quaternary ammonium compounds prepared thereby.Type: GrantFiled: April 19, 1982Date of Patent: October 30, 1984Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Horst Rutzen
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Patent number: 4450295Abstract: Process for manufacturing anhydrous 2-hydroxy-3-chlorophropane trialkylammonium chloride by conversion of trialkylammonium chloride with epichlorohydrin by forming an aqueous solution of trialkylammonium chloride in an organic solvent inert to epichlorohydrin, the solvent forming an azeotrope with ater which boils at temperatures up to the normal boiling point of the solvent, distilling off the azeotrope to form a suspension of trialkylammonium chloride in the solvent reaction product and reacting the reaction product in the solvent with epuichlorohydrin at a temperature of 20.degree. to 120.degree. C.Type: GrantFiled: December 18, 1981Date of Patent: May 22, 1984Assignee: Chemische Fabriek Zaltbommel, B.V.Inventor: Hendrikus J. H. van der Mass
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Patent number: 4441884Abstract: The present invention relates to a process for treating a polyamide textile substrate to increase the affinity thereof for anionic dyes or to reserve the same against cationic dyes comprising applying thereto, in a weakly alkaline medium, a compound of formula I, ##STR1## wherein R is phenyl; naphthyl; (C.sub.5-6)cycloalkyl; or phenyl or naphthyl substituted by a total of up to 3 substituents selected from the group consisting of (C.sub.1-4)alkyl, chlorine and bromine (maximum of two of each of these);each of R.sub.1 and R.sub.2, independently, is (C.sub.1-4)alkyl, and X.sup..crclbar. is a non-chromophoric anion.Type: GrantFiled: November 9, 1978Date of Patent: April 10, 1984Assignee: Sandoz Ltd.Inventors: Hans-Peter Baumann, Urs Mosimann
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Patent number: 4421932Abstract: Process for the manufacture of quaternary ammonium compounds by reacting a compound having a terminal epoxy group with a tertiary amine which is partly present as the free amine and partly present in the form of a salt, followed by the addition of sufficient acid at the end of the reaction to complete salt formation of the quaternary ammonium compound.Type: GrantFiled: April 19, 1982Date of Patent: December 20, 1983Assignee: Henkel KGaAInventors: Horst Rutzen, Manfred Petzold
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Patent number: 4401577Abstract: This disclosure relates to fabric softening compositions containing quaternary ammonium dihydroborates and to methods of softening textiles employing such compounds and compositions. Such softening compositions have unusually and unexpectedly favorable stabilities in 3% dispersions in water.Type: GrantFiled: February 23, 1982Date of Patent: August 30, 1983Assignee: Akzona IncorporatedInventor: James M. Richmond
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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