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)
  • Patent number: 5223628
    Abstract: 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: Grant
    Filed: November 7, 1991
    Date of Patent: June 29, 1993
    Assignee: Sherex Chemical Company, Inc.
    Inventor: David E. Whittlinger
  • Patent number: 5221794
    Abstract: 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: Grant
    Filed: November 7, 1991
    Date of Patent: June 22, 1993
    Assignee: Sherex Chemical Company, Inc.
    Inventors: Jeannene A. Ackerman, Michael Miller, David E. Whittlinger
  • Patent number: 5196418
    Abstract: 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: Grant
    Filed: February 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Board of Supervisors, Louisiana State University Agricultural & Mechanical College
    Inventors: Richard D. Gandour, Gnanasambandam Kumaravel
  • Patent number: 5196582
    Abstract: 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: Grant
    Filed: July 1, 1991
    Date of Patent: March 23, 1993
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, James E. Borland, Jeffrey W. Perine, Joe D. Sauer
  • Patent number: 5171641
    Abstract: 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: Grant
    Filed: July 25, 1990
    Date of Patent: December 15, 1992
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: William P. Roberts, Marvin R. Havens
  • Patent number: 5162048
    Abstract: 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: Grant
    Filed: August 20, 1990
    Date of Patent: November 10, 1992
    Assignee: Kirsten, Inc.
    Inventor: Samuel Diaz-Valdes
  • Patent number: 5152916
    Abstract: 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: Grant
    Filed: August 21, 1990
    Date of Patent: October 6, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hermann Hoffmann, Frederic Mabire
  • Patent number: 5147411
    Abstract: 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: Grant
    Filed: March 11, 1991
    Date of Patent: September 15, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Rosemarie Topfl
  • Patent number: 5137919
    Abstract: 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: Grant
    Filed: December 31, 1990
    Date of Patent: August 11, 1992
    Assignee: Biomembrane Institute
    Inventors: Yasuyuki Igarashi, Mahammad N. Ahmad, Hirofumi Okoshi, Sen-Itiroh Hakomori
  • Patent number: 5136095
    Abstract: 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: Grant
    Filed: December 1, 1988
    Date of Patent: August 4, 1992
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Thomas L. Tarnowski, Cheng-I Lin, Edwin F. Ullman
  • Patent number: 5077435
    Abstract: 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: Grant
    Filed: September 12, 1990
    Date of Patent: December 31, 1991
    Assignee: The Dow Chemical Company
    Inventors: Russell B. Kimbrell, Christian D. Kneupper, Ruben L. Krause
  • Patent number: 5075165
    Abstract: 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: Grant
    Filed: May 11, 1990
    Date of Patent: December 24, 1991
    Assignee: Nissan Motor Company, Ltd.
    Inventors: Hiroyuki Kishi, Hitoshi Kimura, Katsuya Yamamoto, Yoshinobu Tamura, Tsuneo Sakauchi, Masahide Nagaoka, Yoichi Masubuchi, Eisaku Nakatani
  • Patent number: 5068431
    Abstract: 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: Grant
    Filed: May 15, 1989
    Date of Patent: November 26, 1991
    Assignee: Witco Corporation
    Inventors: Anastasios Karalis, Thomas Morong, Charles Juszkiewicz
  • Patent number: 5053531
    Abstract: 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: Grant
    Filed: December 12, 1989
    Date of Patent: October 1, 1991
    Assignee: PPG Industries, Inc.
    Inventor: Cheruthur Govindan
  • Patent number: 5015754
    Abstract: 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: Grant
    Filed: August 21, 1989
    Date of Patent: May 14, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes P. Dix, Rolf Fikentscher, Ingrid Steenken-Richter
  • Patent number: 4997912
    Abstract: 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: Grant
    Filed: December 15, 1988
    Date of Patent: March 5, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Wirtz, Hermann Hoffmann, Werner Ritschel, Manfred Hofinger, Michael Mitzlaff, Dietrich Wolter
  • Patent number: 4992211
    Abstract: 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: Grant
    Filed: November 21, 1989
    Date of Patent: February 12, 1991
    Assignee: Sandoz Ltd.
    Inventor: Robert V. Casciani
  • Patent number: 4983748
    Abstract: 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: Grant
    Filed: December 28, 1988
    Date of Patent: January 8, 1991
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: John J. Tsai, Patrick G. Jobe, Diane J. Lamb, Robert L. Billmrs, Martin M. Tessler
  • Patent number: 4982000
    Abstract: 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: Grant
    Filed: November 3, 1989
    Date of Patent: January 1, 1991
    Assignee: Sherex Chemical Co., Inc.
    Inventors: Gary W. Earl, Owen Portwood
  • Patent number: 4883917
    Abstract: 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: Grant
    Filed: October 1, 1985
    Date of Patent: November 28, 1989
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, Joe D. Sauer, James E. Borland
  • Patent number: 4880894
    Abstract: 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: Grant
    Filed: September 26, 1988
    Date of Patent: November 14, 1989
    Assignee: 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
  • Patent number: 4864060
    Abstract: 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: Grant
    Filed: August 31, 1987
    Date of Patent: September 5, 1989
    Assignee: Witco Corporation
    Inventors: Anastasios Karalis, Thomas Morong, Charles Juszkiewicz
  • Patent number: 4845289
    Abstract: 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: Grant
    Filed: February 29, 1988
    Date of Patent: July 4, 1989
    Assignee: Nalco Chemical Company
    Inventors: Donald G. Ries, Allan W. Smith
  • Patent number: 4843176
    Abstract: 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: Grant
    Filed: October 25, 1985
    Date of Patent: June 27, 1989
    Assignee: Petrolite Corporation
    Inventors: Neil E. S. Thompson, Derek Redmore, Bernardus A. Oude Alink, Benjamin T. Outlaw
  • Patent number: 4836958
    Abstract: 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: Grant
    Filed: July 31, 1986
    Date of Patent: June 6, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanasios Karydas
  • Patent number: 4824602
    Abstract: 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: Grant
    Filed: December 22, 1987
    Date of Patent: April 25, 1989
    Assignee: The Procter & Gamble Company
    Inventor: Prem S. Juneja
  • Patent number: 4814506
    Abstract: 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: Grant
    Filed: August 21, 1987
    Date of Patent: March 21, 1989
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kazuhiko Katayama, Shigeki Hamaguchi, Yoshikazu Kogame, Takehisa Ohashi, Kiyoshi Watanabe
  • Patent number: 4812263
    Abstract: Described are bis-quaternary ammonium compounds of 2-hydroxypropylene, e.g., 2-hydroxy propylene-1,3-bis(dimethyl stearyl ammonium chloride).
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: March 14, 1989
    Assignee: PPG Industries, Inc.
    Inventor: Robert B. Login
  • Patent number: 4778813
    Abstract: 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: Grant
    Filed: January 30, 1985
    Date of Patent: October 18, 1988
    Assignee: Buckman Laboratories International, Inc.
    Inventors: Joseph G. Fenyes, John D. Pera
  • Patent number: 4764306
    Abstract: 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: Grant
    Filed: August 22, 1986
    Date of Patent: August 16, 1988
    Assignee: PPG Industries, Inc.
    Inventor: Robert B. Login
  • Patent number: 4722978
    Abstract: 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: Grant
    Filed: August 30, 1985
    Date of Patent: February 2, 1988
    Assignee: The B. F. Goodrich Company
    Inventor: Simon H. Yu
  • Patent number: 4709083
    Abstract: 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: Grant
    Filed: May 19, 1986
    Date of Patent: November 24, 1987
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Bernard F. Spielvogel
  • Patent number: 4692543
    Abstract: 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: Grant
    Filed: February 25, 1986
    Date of Patent: September 8, 1987
    Assignee: Lonza Ltd.
    Inventors: Leander Tenud, Jacques Gosteli
  • Patent number: 4675180
    Abstract: 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: Grant
    Filed: February 18, 1986
    Date of Patent: June 23, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Franz Gunter
  • Patent number: 4661634
    Abstract: 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: Grant
    Filed: September 16, 1985
    Date of Patent: April 28, 1987
    Assignee: The Dow Chemical Company
    Inventors: Walter L. Vaughn, Milton S. Wing
  • Patent number: 4638089
    Abstract: 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: Grant
    Filed: April 24, 1981
    Date of Patent: January 20, 1987
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Iwao Hisamoto, Chiaki Maeda, Mitsuhiro Nishiwaki
  • Patent number: 4602110
    Abstract: 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: Grant
    Filed: May 15, 1985
    Date of Patent: July 22, 1986
    Assignee: The Dow Chemical Company
    Inventor: Emmett L. Tasset
  • Patent number: 4594452
    Abstract: 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: Grant
    Filed: June 24, 1985
    Date of Patent: June 10, 1986
    Assignee: Allied Corporation
    Inventors: Herbert K. Reimschuessel, Michael A. Kocur
  • Patent number: 4540521
    Abstract: 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: Grant
    Filed: January 16, 1984
    Date of Patent: September 10, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventors: Roger H. Garst, Frank N. Tuller, Charles R. Tucker
  • Patent number: 4540725
    Abstract: 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: Grant
    Filed: August 15, 1984
    Date of Patent: September 10, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Robert D. Jerabek, Jeffrey G. Koren, Mark W. Johnson
  • Patent number: 4505839
    Abstract: Polyalkanolamines of controlled molecular weights and their uses as demulsifiers and/or flotation agents.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: March 19, 1985
    Assignee: Petrolite Corporation
    Inventors: Thomas J. Bellos, Eva G. Lovett
  • Patent number: 4492802
    Abstract: 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: Grant
    Filed: April 19, 1982
    Date of Patent: January 8, 1985
    Assignees: Henkel Kommanditgesellschaft auf Aktien, Degussa Aktiengesellschaft
    Inventors: Horst Rutzen, Peter Nikolaus, Martin Bischoff, Rudolf Lehmann
  • Patent number: 4485259
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: November 27, 1984
    Assignee: PPG Industries, Inc.
    Inventors: Robert D. Jerabek, Jeffrey G. Koren, Mark W. Johnson
  • Patent number: 4482713
    Abstract: 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: Grant
    Filed: July 1, 1982
    Date of Patent: November 13, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Rainer Strickler
  • Patent number: 4480126
    Abstract: 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: Grant
    Filed: April 19, 1982
    Date of Patent: October 30, 1984
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Horst Rutzen
  • Patent number: 4450295
    Abstract: 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: Grant
    Filed: December 18, 1981
    Date of Patent: May 22, 1984
    Assignee: Chemische Fabriek Zaltbommel, B.V.
    Inventor: Hendrikus J. H. van der Mass
  • Patent number: 4441884
    Abstract: 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: Grant
    Filed: November 9, 1978
    Date of Patent: April 10, 1984
    Assignee: Sandoz Ltd.
    Inventors: Hans-Peter Baumann, Urs Mosimann
  • Patent number: 4421932
    Abstract: 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: Grant
    Filed: April 19, 1982
    Date of Patent: December 20, 1983
    Assignee: Henkel KGaA
    Inventors: Horst Rutzen, Manfred Petzold
  • Patent number: 4401577
    Abstract: 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: Grant
    Filed: February 23, 1982
    Date of Patent: August 30, 1983
    Assignee: Akzona Incorporated
    Inventor: James M. Richmond
  • Patent number: 4399077
    Abstract: 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: Grant
    Filed: June 4, 1980
    Date of Patent: August 16, 1983
    Assignee: L'Oreal
    Inventors: Guy Vanlerberghe, Henri Sebag