Q Is Hydrogen Or A Lower Saturated Alkyl Substituent Patents (Class 564/215)
  • Patent number: 5391578
    Abstract: N-lower alkyl neoalkanamides are liquid state isomeric mixtures. Such new compounds are mixtures of isomeric secondary amides which have insect repellent properties, being especially effective against German cockroaches. They may be applied directly to surfaces to be treated and have been found to be sufficiently substantive to such surfaces so as to impart insect repelling properties thereto.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: February 21, 1995
    Assignee: Colgate-Palmolive Co.
    Inventor: Robert J. Steltenkamp
  • Patent number: 5359082
    Abstract: A process for the preparation of 4-substituted imidazoles of the general formula ##STR1## in which R denotes C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.20 cycloalkyl, aryl, and C.sub.7 -C.sub.20 aralkyl,whereina) N-formyl-.alpha.-aminonitriles of the general formula I ##STR2## in which R has the meanings stated above and A stands for carbonyl, are reacted, at a temperature ranging from 20.degree. to 200.degree. C. and a pressure ranging from 20 to 500 bar, with hydrogen in the presence of hydrogenation catalysts andb) the resulting N-formyl-1,2-diamines of the general formula ##STR3## in which R and A have the meanings stated above and n stands for 0 or 1, are reacted over a cyclization/dehydrogenation catalyst at a temperature ranging from 200.degree. to 600.degree. C. and a pressure ranging from 0.001 to 5 bar.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: October 25, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Koehler, Thomas-Michael Kahl, Horst Neuhauser, Hardo Siegel, Michael Kroener
  • Patent number: 5349109
    Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).
    Type: Grant
    Filed: August 26, 1993
    Date of Patent: September 20, 1994
    Assignee: The Board of Regents of the University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5326909
    Abstract: A method of stabilizing N-vinylformamide, which may contain customary polymerization inhibitors, against polymerization during storage or transport, comprises adding to the N-vinylformamide monomers of the general formula ##STR1## where R+H, CH.sub.3 ##STR2## R.sup.2 +C.sub.1 -C.sub.4 -alkyl, as stabilizer in amounts of from 1 to 99 .degree.6 by weight, based on the mixture.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: July 5, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Kroener, Jacques Dupuis
  • Patent number: 5319133
    Abstract: The present invention relates to a process for preparation of an isocyanate comprising (a) reacting an amide with an aqueous solution of hypochlorous acid in the presence of an water-immiscible organic solvent to produce an N-chloro amide; and (b) reacting said N-chloro amide with a base in the presence of a phase transfer catalyst and a water immiscible organic solvent to produce an isocyanate.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: June 7, 1994
    Assignee: Olin Corporation
    Inventors: Robert J. Raynor, Thomas A. Knowles
  • Patent number: 5312966
    Abstract: There is disclosed a process for efficiently producing a carboxylic acid ester and formamide by reacting a carboxylic acid amide with a formic acid ester or with an alcohol and carbon monoxide in the presence of a strongly basic anion-exchange resin. By the use of the strongly basic anion-exchange resin as the catalyst, the process of the present invention enables the efficient production of the carboxylic acid ester as well as formamide from the Carboxylic acid amide and Formic acid ester, etc. with a high selectivity under mild reaction conditions and facilitates the separation of the catalyst from the reaction product, thereby greatly enhancing the industrial significance of itself.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: May 17, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Abe, Yoshiyuki Nishide, Nobuyuki Muro, Hirofumi Higuchi
  • Patent number: 5292952
    Abstract: Disclosed is a process for producing 2-fluoro-4-(trifluoromethyl) acetanilide which comprises reacting 3,4-difluorobenzotrifluoride with acetamide in the presence of a base in an aprotic polar solvent or in a mixture of an aprotic polar solvent and an aprotic non-polar solvent.
    Type: Grant
    Filed: November 19, 1992
    Date of Patent: March 8, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Toshiaki Taki, Noritada Matsuo
  • Patent number: 5284650
    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 5, 1992
    Date of Patent: February 8, 1994
    Assignee: Sherex Chemical Co., Inc.
    Inventor: David E. Whittlinger
  • Patent number: 5278341
    Abstract: The invention relates to N-acyl-aminoalkyl-2-hydroxyethylsulfides of formula R--CONH--(CH.sub.2).sub.n --S--CH.sub.2 --CH.sub.2 --OH, where R is a hydrogen atom or a (C.sub.1 -C.sub.4) alkyl group and n is an integer between 3 and 6, and to a method for preparing them. The method consists in reacting compounds of formula R--CONH--(CH.sub.2).sub.m --CH.dbd.CH.sub.2, where R has the above-mentioned meaning and m is an integer between 1 and 4, with the equivalent quantity of mercaptoethanol at approximately 15.degree. to approximately 150.degree. C. in the presence of a radical starter and in the presence or in the absence of a solvent which is inert to the reactants and to radical reactions.
    Type: Grant
    Filed: September 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Meier, Heinrich Angenendt, Peter Mischke
  • Patent number: 5270310
    Abstract: The present invention provides methods for inhibiting protein kinase C which comprise contacting protein kinase C with an inhibitory amount of a compound having the formula ##STR1## wherein R.sub.1 is C.sub.8 through C.sub.15 alkyl; R.sub.2 is H, C.sub.1 through C.sub.10 alkyl, or benzyl; R.sub.3 is N-heterocyclic, N-alkylheterocyclic, quaternized N-heterocyclic, NR.sub.4 R.sub.5 or N.sup.+ R.sub.4 R.sub.5 R.sub.6 X.sup.- ; R.sub.4, R.sub.5 and R.sub.6 are independently C.sub.1 through C.sub.10 alkyl; n is 2, 3, 4, or 5; and X is an anion. The invention also provides novel compounds having the formula ##STR2## wherein R.sub.1 is C.sub.8 through C.sub.15 alkyl; R.sub.2 is H, C.sub.1 through C.sub.10 alkyl, or benzyl; R.sub.3 is N-heterocyclic, N-alkylheterocyclic or quaternized N-heterocyclic; and n is 2, 3, 4, or 5.
    Type: Grant
    Filed: December 13, 1991
    Date of Patent: December 14, 1993
    Assignees: Sphinx Pharmaceuticals Corporation, Duke University
    Inventors: Robert M. Bell, Robert J. Fogelsong, Jeffrey B. Nichols
  • Patent number: 5254684
    Abstract: A process for producing an amide which comprises subjecting an oxime to liquid phase rearrangement in the presence of phosphorus pentoxide and at least one compound selected from the group consisting of N,N-dialkyl amides, N-alkyl cyclic amides and dialkyl sulfoxides and optionally a fluorine-containing strong said or its derivative. Said process can rearrange an oxime to a corresponding amide in a good yield under mild reaction conditions in the presence of a less stoichiometric amount of a catalyst.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: October 19, 1993
    Assignees: Sumitomo Chemical Company, Limited, Yusuke Izumi
    Inventors: Yusuke Izumi, Hiroshi Sato, Hiroshi Yoshioka, Yoshisaburou Nomura
  • Patent number: 5225547
    Abstract: A reaction accelerator for rearrangement of an oxime to an amide consisting of an alkylating agent and an N,N-disubstituted formamide or N,N-disubstituted carboxylic acid amide represented by formula (1): ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, represent alkyl groups having 1 to 6 carbon atoms or substituted or unsubstituted phenyl groups having 6 to 9 carbon atoms, and R.sup.3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. An amide can effectively be produced by rearranging a corresponding oxime in the presence of said reaction accelerator.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: July 6, 1993
    Assignees: Sumitomo Chemical Company Limited, Yusuke Izumi
    Inventor: Yusuke Izumi
  • 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: 5185465
    Abstract: Novel 4-phenyl-1,3-benzodiazepines and 2-amino-.alpha.-phenylphenethylamines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants. The 2-amino-.alpha.-phenylphenethylamines are useful as anticonvulsant and neuroprotective agents.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: February 9, 1993
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
  • Patent number: 5183923
    Abstract: The invention concerns a method for the preparation of polyurethane, polyester, polyamide, and polyurea diols which contain essentially all primary hydroxyl groups without capping by ethylene oxide. The method comprises coupling an alkylene oxide adduct of propylene glycol t-butyl ether or butylene glycol t-butyl ether or its aminated derivative with organic diisocyanates or dibasic acids followed by cleavage of the t-butyl group with an acid catalyst.The resulting diol is useful in many types of urethane applications including foams, elastomers and coatings.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: February 2, 1993
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, George P. Speranza
  • Patent number: 5180851
    Abstract: This invention relates to an improved process for the formation of N-(l-alkoxyalkyl)amides with coproduction of alkylidene bisamides. The N-(l-alkoxyalkyl)formamides of this invention are prepared by reacting formamide with an acetal or hemiacetal carboxylate ester represented by the formulas below in the presence of a solid acid ion exchange resin wherein the acid groups have been neutralized with an amine compound having a pKa (as the protonated amine in water) from about 4 to 9. The hemiacetal ester is represented by formula I and the acetal is represented by formula II. ##STR1## In the above formulas, R is C.sub.1 -C.sub.8 alkyl, aralkyl or aryl; R.sub.1 and R.sub.2 are C.sub.1 -C.sub.8 alkyl, or aryl; and R.sub.3 is secondary or tertiary alkyl having from 3-8 carbon atoms.
    Type: Grant
    Filed: March 21, 1991
    Date of Patent: January 19, 1993
    Assignee: Air Products and Chemicals Inc.
    Inventors: Mark L. Listemann, Robert K. Pinschmidt, Jr.
  • Patent number: 5160648
    Abstract: Improved additives/detergents for lubricant and fuel compositions are obtained by condensing a hydroxyalkyl or hydroxyaryl compound with an amine compound. The condensates according to the present invention are produced by the acid catalyzed condensation of the amine reactant with the hydroxy reactant.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: November 3, 1992
    Assignee: The Lubrizol Corporation
    Inventor: Thomas F. Steckel
  • Patent number: 5128471
    Abstract: The present invention relates to a process for the production of primary amines containing aliphatically or cycloaliphatically bound amino groups, characterized in that the isocyanate groups of organic isocyanates containing aliphatically and/or cycloaliphatically bound isocyanate groups are formylated with formic acid in a first reaction step and the N-formyl groups are subsequently converted into amino groups.The present invention also relates to polyamine mixtures obtained by this process and containinga) about 40 to 90% by weight, based on the total weight of components a) and b), of N,N',N"-tris-(6-aminohexyl)-isocyanurate andb) about 10 to 60% by weight, based on the total weight of components a) and b), of higher homologs of this triamine containing more than one isocyanurate ring.Finally, the present invention relates to the use of these polyamine mixtures as hardeners for polymer precursors containing epoxide or isocyanate groups.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: July 7, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans J. Scholl
  • Patent number: 5118845
    Abstract: This invention relates to a method administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structural formula ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of alkyl radicals and cycloalkyl radicals comprising from 1 to 20 carbon atoms and R is selected from the group consisting of alkyl radicals and cycloalkyl radicals comprising from 1 to 30 carbon atoms; provided, however, that the total number of carbon atoms in said compound is 15 or more and the total number of carbon atoms in R.sup.1 and R.sup.2 is 5 or more.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: June 2, 1992
    Assignee: Whitby Research, Inc.
    Inventors: James V. Peck, Gevork Minaskanian
  • Patent number: 5118852
    Abstract: 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 an amido compound containing a --CO.NH-- group.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: June 2, 1992
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, James E. Borland, Joe D. Sauer
  • Patent number: 5118846
    Abstract: Disclosed is a method which comprises introducing into a reaction zone a feed which comprises a hydroxyl compound reactant, R"OH at least one amide reactant selected from R--CONH.sub.2 and R--CONHR', and a Lewis base as catalyst, thereby reacting R"OH with said amide reactant to produce a reaction mixture containing at least one disubstituted amide selected from R--CONR".sub.2 and R--CONR'R", whereineach of R, R' and R" contains no acetylenic unsaturation and 1 to 30 carbon atoms;each of R, R' and R" is selected from a hydrocarbyl groups and a hydrocarbyl group that is substituted with a group selected from carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, and hydroxyl.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: June 2, 1992
    Assignee: The Standard Oil Company
    Inventor: Mark C. Cesa
  • Patent number: 5107022
    Abstract: The invention relates to a process for the preparation of compounds of formula ##STR1## wherein R is unsubstituted or substituted C.sub.1 -C.sub.4 alkyl or unsubstituted or substituted phenyl, X is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl, and Y is unsubstituted or substituted C.sub.1 -C.sub.4 alkyl, which process comprises subjecting compounds of formula ##STR2## wherein R, X and Y are as defined for formula I, to catalytic hydrogenation in the alkaline pH range.The compounds obtained by the process of this invention are suitable intermediates for the synthesis of dyes.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: April 21, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Amaury P. de Besset
  • Patent number: 5103055
    Abstract: Disclosed is a method which comprises the reaction in a reaction zone of a nitrile, RCN, with a hydroxyl compound, R'OH, in the presence of water introduced into the reaction zone in the amount of more than 0.15 mole and up to 10 moles, per mole of RCN introduced to the reaction zone, thereby producing a reaction mixture containing at least one amide selected from R--CONHR' and R--CON(R').sub.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: April 7, 1992
    Assignee: The Standard Oil Company
    Inventor: Mark C. Cesa
  • Patent number: 5072024
    Abstract: Disclosed is a method which comprises the reaction in a reaction zone of a nitrile, RCN, with a hydroxyl compound, R'OH, in the presence of an inorganic catalyst introduced into the reaction zone, thereby producing a reaction mixture containing at least one amide selected from R--CONHR' and R--CON(R').sub.2, whereineach of R and R' contains no acetylenic unsaturation and 1 to 30 carbon atoms,each of R and R' is independently selected from a hydrocarbyl group and a hydrocarbyl group that is substituted with a group selected from cyano, carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, and hydroxyl,wherein said inorganic catalyst is selected from phosphates and sulfates of Be, Ng, Al and B, and mixtures thereof.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: December 10, 1991
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Sandra L. Denman
  • Patent number: 5059713
    Abstract: N-vinyl amides having the general structural formula:CH.sub.2 =CH--NHCOR.sup.1wherein R.sup.1 is hydrogen, a C.sub.1 to C.sub.6 alkyl group or a C.sub.6 -C.sub.9 aryl or substituted aryl group, are formed by cracking carboxylic acid amides having the general structure formula: ##STR1## wherein R.sup.1 is as described above, and R.sup.2 is a C.sub.1 to C.sub.9 alkoxy, carboxy or carboxamide group. Said carboxylic acid amides are cracked by heating, to a temperature of about 210.degree.-350.degree. C., in the presence of a catalyst comprising MgS or an oxide or mixed oxide of Ca or Sr.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: October 22, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John N. Armor, Gene E. Parris
  • Patent number: 5041660
    Abstract: Disclosed is a novel .alpha.-chloroketone derivative as a synthesis intermediate of N-cyano-N'-methyl-N"-(2-((5-methyl-1H-imidazol-4-yl)methylthio)ethyl)guani dine (general name: Cimetidine) which shows an action of controlling the secretion of gastric acid and is valuable as a medicine for remedy of a gastric ulcer. This .alpha.-chloroketone derivative is prepared by reacting disulfide derivative with sulfuryl chloride and reacting the reaction product with methylvinyl ketone or by reacting a mercapto derivative with 3-chloro-3-buten-2-one.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: August 20, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Keiichi Yokoyama, Yoshio Noguchi, Noriaki Kihara
  • Patent number: 5041659
    Abstract: Disclosed is a method which comprises introducing into a reaction zone a feed which comprises a hydroxyl compound reactant, R"OH, at least one amide reactant selected from R-CONH.sub.2 and R-CONHR', and an inorganic catalyst, thereby reacting R"OH with said amide reactant to produce a rection mixture containing at least one disubstituted amide selected from R-CONHR".sub.2 and R-CONHR'R", whereineach of R, R' and R" contains no acetylenic unsaturation and 1 to 30 carbon atoms,each of R, R' and R" is selected from a hydrocarbyl group and a hydrocarbyl group that is substituted with a group selected from carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, and hydroxyl,wherein said inorganic catalyst is selected from phosphates and sulfates of a Group 13 element and of a Group 2 metal having an atomic weight less than 145, and mixtures thereof.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: August 20, 1991
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Sandra L. Denman
  • Patent number: 5015773
    Abstract: An amine is produced by reacting in the presence of hydrogen at elevated temperature a first reactant which is a compound substantially involatile at the elevated temperature employed and having either one, two or more hydroxyl functions, each of which is independently either a primary or secondary hydroxyl function, with a second reactant which is either ammonia or a primary or a secondary amine in the presence of a reductive amination catalyst wherein the reaction is effected in either a continuously or periodically open system.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: May 14, 1991
    Assignee: BP Chemicals Limited
    Inventor: Ian D. Dobson
  • Patent number: 5011854
    Abstract: A hydroxamic acid compound represented by the general formula (I) or a salt thereof; ##STR1## wherein R.sup.1 represents a hydrogen atom, or a substituted or unsubstituted alkanoyl group, R.sup.2 represents an unsubstituted alkanoyl, substituted lower alkanoyl or substituted lower alkyl group, and m represents an integer of 3 to 7, which are useful for the prevention and/or treatment of diseases caused by lipoxygenase-mediated metablites.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: April 30, 1991
    Assignee: Kyowa Hakko Kogyo Co. Ltd.
    Inventors: Mitsuru Takahashi, Shigeto Kitamura, Hiroshi Kase, Masaji Kasai, Isao Kawamoto, Takao Iida, Hiroshi Sano, Hiromitsu Saito, Koji Yamada, Chikara Murakata
  • Patent number: 4983757
    Abstract: Carboxylic acid esters and formamide are efficiently obtained for reacting carboxylic acid amides and formic acid esters, or carboxylic acid amides, alcohols and carbon monoxide in the presence of an alkaline earth metal oxide catalyst.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: January 8, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Jiro Ishikawa, Hirofumi Higuchi, Shuji Ebata, Koichi Kida
  • Patent number: 4982006
    Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 1, 1991
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventor: Thomas T. Hudec
  • Patent number: 4958005
    Abstract: A fluorine-containing composition represented by formula (I) ##STR1## wherein X represents a group containing a polyfluoroaliphatic group having from 3 to 26 carbon atoms; R represents a hydrogen atom or an aliphatic group having from 1 to 3 carbon atoms; n represents an integer of from 2 to 3; p represents an integer of from 1 to 100; and Y represents a group represented by formula (II) or formula (III) ##STR2## wherein R represents a hydrogen atom or an aliphatic group having from 1 to 3 carbon atoms; n represents an integer of from 2 to 3; and Z represents an iodine atom, a sulfonate group, or a sulfate group, ##STR3## wherein R represents a hydrogen atom or an aliphatic group having from 1 to 3 carbon atoms; n represents an integer of from 2 to 3; and Z.sup.1 represents an iodine atom, a bromine atom, a chlorine atom, or a hydroxyl group; and a process for preparing the same.
    Type: Grant
    Filed: September 20, 1988
    Date of Patent: September 18, 1990
    Assignee: Daikin Industries, Ltd.
    Inventors: Takeo Saegusa, Masatoshi Miyamoto, Yoshiyuki Sano
  • Patent number: 4942259
    Abstract: N-vinyl amides having the general structural formula:CH.sub.2 .dbd.CH--NHCOR.sup.1wherein R.sup.1 is hydrogen, a C.sub.1 to C.sub.6 alkyl group or C.sub.6 -C.sub.9 aryl or substituted aryl group, are formed by cracking carboxylic acid amides having the general structure formula: ##STR1## wherein R.sup.1 is as described above, and R.sup.2 is a C.sub.1 to C.sub.9 alkoxy, carboxy or carboxamide group. Said carboxylic acid amides are cracked by heating, to a temperature of about 150.degree.-350.degree. C., in the presence of a porous, hydrogen-abstracting catalyst.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: July 17, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gene E. Parris, John N. Armor
  • Patent number: 4923952
    Abstract: The present invention is directed to monoformylated 3,3'-diaminodipropylamine mixtures corresponding to formulae I and II ##STR1## The present invention is also directed to a process for the production of these mixtures by reacting acrylonitrile and formamide in the presence of a 4-aminopyridine derivative to form N,N-bis-(2-cyanoethyl)-formamide which is then hydrogenated to the monoformylated 3,3'-diaminopropylamine mixture corresponding to formulae I and II.Finally, the present invention is also directed to the use of these mixtures as chain extending agents for the preparation of polyurethanes by the polyisocyanate polyaddition process.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: May 8, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Helmut Reiff
  • Patent number: 4922016
    Abstract: N-(sulfonylmethyl)formamides are obtained by reacting a sulfinic acid, formaldehyde and formamide in the presence of a second acid and a controlled amount of water. The formamides can be converted to the corresponding sulfonylmethylisocyanides.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: May 1, 1990
    Assignee: Gist-Brocades N.V.
    Inventor: Nicolaas C. M. E. Barendse
  • Patent number: 4906777
    Abstract: Ethylidene bis-formamide, a precursor for the monomer N-vinylformamide, is made in high yield by heating together formamide and acetaldehyde in a mol ratio of at least 3:1 and in a reaction mixture which is at least 20 weight percent formic acid. In a preferred procedure the acetaldehyde is added after the formamide has been preheated and formic acid is present. Yields of ethylidene bis-formamide of over 50%, based on the acetaldehyde, are obtained in relatively short reaction times, before loss of substantial amounts of recoverable formamide through hydrolysis.
    Type: Grant
    Filed: October 19, 1988
    Date of Patent: March 6, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Robert K. Pinschmidt, Jr., Andrew F. Nordquist
  • Patent number: 4886910
    Abstract: The present invention provides a cyanoguanidine derivtive which is a precursor for the synthesis of N-cyano-N'-methyl-N"-[2-{(5-methyl-1H-imidazol-4-yl)methylothio}ethyl]-gua nidine (Cimetidine) or its relted compound, which has an action of controlling secretion of acid in the stomach based on the histamine H.sub.2 receptor antagonism and is valuable as a drug for treating gastric ulcer. This cyanoguanidine derivative is prepared by reacting a haloketone derivative with an ammonium salt and a lower fatty acid salt or by reacting other cyanoguanidine derivative with an ammonium salt.
    Type: Grant
    Filed: February 17, 1988
    Date of Patent: December 12, 1989
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hiroaki Tan, Koji Kato, Junichi Imuta, Noriaki Kihara
  • Patent number: 4886800
    Abstract: The present invention comprises certain amide and ester derivatives of 4-substituted-cinnoline-3-carboxylic acids and 3-acyl-4-substituted-cinnoline derivatives, and their use as central nervous system (CNS) depressants.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: December 12, 1989
    Assignee: ICI Americas Inc.
    Inventor: James F. Resch
  • Patent number: 4872902
    Abstract: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: October 10, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4871858
    Abstract: An amine is reached with dimethyformamioe in the presence of a solid catalyst to produce a formamide corresponding to the amine. The solid catalyst includes an oxide of metals belonging to Groups III, IV and V of the Periodic Table.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: October 3, 1989
    Assignee: Japan Tobacco Inc.
    Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
  • Patent number: 4869728
    Abstract: A motor fuel composition which inhibits engine ORI comprises a mixture of hydrocarbons boiling in the range of 90.degree. F.-450.degree. F. and the reaction product of one or more substituted or unsubstituted aliphatic carboxylic acids, including acyl-containing aliphatic carboxylic acids, and a polyoxyalkylene diamine.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: September 26, 1989
    Assignee: Texaco Inc.
    Inventor: Rodney L. Sung
  • Patent number: 4859776
    Abstract: A process for the preparation of enantiomerically homogeneous aminopyrrolidinyl naphthyridine carboxylic acids and quinolone carboxylic acids, and for the preparation of intermediates that are useful in the production of these carboxylic acids. The compounds are useful as anti-bacterials.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: August 22, 1989
    Assignee: Abbott Laboratories
    Inventors: Daniel T. Chu, Terry J. Rosen
  • Patent number: 4855292
    Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: August 8, 1989
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
  • Patent number: 4855498
    Abstract: Disclosed are platinum (IV) chelates derived from substituted amides. The chelates result from the reaction under mild conditions of potassium chloroplatinate (II) and the appropriate amide. The chelate transdichloro-cis-bis(dimethylacetamide-C,O) was prepared, fully characterized and exemplified in preparation of the antihistamine diphenhydramine hydrochloride.
    Type: Grant
    Filed: February 22, 1988
    Date of Patent: August 8, 1989
    Assignee: University of Delaware
    Inventors: Rosette M. Roat, Seymour Yolles
  • Patent number: 4853485
    Abstract: Monomethylformamide and dimethylformamide are produced by the catalytic reaction of formamide and methanol, using a quaternary ammonium compound as the catalyst.
    Type: Grant
    Filed: October 21, 1987
    Date of Patent: August 1, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Harold E. Bellis
  • Patent number: 4822483
    Abstract: A collector composition for use in froth flotation processes comprises two collectors. One of the collectors is preferably an N-(hydrocarbyl)-alpha, omega-alkanediamine, an (omega-aminoalkyl) hydrocarbon amide or mixture thereof. The second collector is a thiocarbonate, a thionocarbamate, a thiophosphate, thiocarbinilide, thiophosphinate, mercaptan, xanthogen formate, xanthic ester or mixture thereof. The collector composition floats a broad range of metal-containing minerals.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: April 18, 1989
    Assignee: The Dow Chemical Company
    Inventors: Richard R. Klimpel, Robert D. Hansen
  • Patent number: 4762949
    Abstract: Synthetically produced substantially pure biologically active compounds having the general formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.20 alkyl, alkenyl, aryl, aralkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkenyl, alkylcycloalkenyl, or cycloalkenylalkyl;R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl or an amide-substituted alkyl having up to 10 carbon atoms;R.sub.3 is a cyclic, straight or branched chain hydrocarbon group having 2-12 carbon atoms, particularly --(CH.sub.2).sub.n --, wherein n is 2-12; orR.sub.2 and R.sub.3 are linked together to form an alkylene chain; andR.sub.4 is selected from ##STR2## (substituted or unsubstituted carbamimidoyl), ##STR3## (dimethylpyrimidyl), or ##STR4## (carbamyl) wherein each of R.sub.5, R.sub.6, and R.sub.7 is hydrogen or the same or different C.sub.1 -C.sub.8 alkyl group. The compounds are useful as bactericides for a wide variety of bacteria, including S.pyogenes, B.subtilis, K.pneumoniae, M.avium, B.fragilis, C.perfringens and C.albicans.
    Type: Grant
    Filed: January 24, 1983
    Date of Patent: August 9, 1988
    Assignee: University of Illinois Foundation
    Inventors: Kenneth L. Rinehart, Jr., Guy T. Carter, Michael T. Cheng
  • Patent number: 4762548
    Abstract: Herbicidally active thiolcarbamates are employed in combination with a certain amide extender compound, the latter in sufficient quantity to minimize soil degradation and to prolong the soil life of the former. As a result, the herbicidal effectiveness of the thiolcarbamate herbicide is significantly enhanced and prolonged, rendering a single application or multiple applications of the herbicide effective over a longer period of time. Such herbicidal compositions can optionally contain a non-phytotoxic antidotally effective amount of thiolcarbamate herbicide antidote.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: August 9, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Reed A. Gray, Ferenc M. Pallos
  • Patent number: 4762829
    Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.
    Type: Grant
    Filed: October 23, 1986
    Date of Patent: August 9, 1988
    Assignee: Eisai Co., Ltd.
    Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura