Polycarboxylic Acid Patents (Class 560/176)
  • Patent number: 5997610
    Abstract: The invention concerns amphiphilic compounds of general formula (I) ##STR1## with at least two hydrophilic and at least two hydrophobic groups based on diacarboxylic acid diamides. The amphiphilic compounds according to the invention are mostly surface-active and are suitable for use as emulsifiers, demulsifiers, detergents, dispergents and hydrotropic agents in industry and households, for example, in the treatment of metals, ore processing, surface finishing, washing, cleaning, cosmetics, medicine and food processing and preparation.
    Type: Grant
    Filed: August 18, 1997
    Date of Patent: December 7, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Klaus Kwetkat, Wulf Ruback
  • Patent number: 5932761
    Abstract: It is provided a process for industrially advantageously producing a branched aldehyde represented by the formula; ##STR1## ?wherein Y represents an acyl group of two or more carbon atoms; and X represents an acyloxymethyl group represented by --CH.sub.2 OY' (where Y' represents an acyl group of two or more carbon atoms), cyano group or an alkoxycarbonyl group! which is useful as an intermediate for pharmaceuticals and agricultural chemicals, comprising subjecting an olefinic compound represented by the following formula; ##STR2## (wherein Y and X are the same as defined above), to the reaction with hydrogen and carbon monoxide in the presence of a rhodium compound and a tertiary organic phosphorus compound with an electronic parameter (.upsilon.-value) of 2080 to 2090 cm.sup.-1 or with a steric parameter (.theta.-value) of 150 to 180.degree..
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: August 3, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshihiro Omatsu, Masahiko Kitayama, Takashi Onishi
  • Patent number: 5837782
    Abstract: A novel bis(mono- or diperoxyoxalate) composition of Structure A, ##STR1## and use of the novel bis(mono- or diperoxyoxalate) composition as an initiators for curing of unsaturated polyester resins and for polymerizing ethylenically unsaturated monomers are disclosed.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: November 17, 1998
    Assignee: Elf Atochem North America, Inc.
    Inventor: Jose Sanchez
  • Patent number: 5767292
    Abstract: The present invention relates to processes for preparing 1-methoxy-2-propyl 3-(7-diethylamino-2-oxo-2H-chromen-3-yl)-3-oxopropionate of the formula I ##STR1## and also di(1-methoxy-2-propyl) acetonedicarboxylate as intermediate for one of the processes.
    Type: Grant
    Filed: May 22, 1997
    Date of Patent: June 16, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Koch, Wolfgang Bauer
  • Patent number: 5736274
    Abstract: A polymer containing a recurring unit of a conjugated N-fluoropyridinium salt and an active material for a positive electrode, an electrolyte, a battery material for the positive electrode and a battery which use such a polymer. That polymer provides a battery material and a primary battery or a secondary battery which have high electromotive force, high energy density, high environmental acceptability, a low internal resistance in charging and discharging and strong recoverability of the electromotive force, and can be useful as a fluorinating agent.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: April 7, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Teruo Umemoto, Kenji Adachi, Ginjiro Tomizawa, Sumi Ishihara, Masayuki Nagayoshi
  • Patent number: 5679830
    Abstract: A pivaloylacetic acid ester is prepared at a high yield by decarbonylating a pivaloylpyruvic acid ester in gas or liquid phase in the presence of an inorganic oxide catalyst which comprises aluminum in an amount of 10% by weight or more in terms of aluminum oxide, and preferably is substantially free from heavy metals, for example, Fe, Cu, Ni, Mn, Cr, Mo and Co, and exhibits a high catalytic activity and chemical stability.
    Type: Grant
    Filed: July 12, 1995
    Date of Patent: October 21, 1997
    Assignee: Ube Industries, Ltd.
    Inventors: Katsuhiko Mizutare, Masayoshi Oku, Tsuyoshi Ueyama
  • Patent number: 5667901
    Abstract: Provided are various 2-acetylglutarate esters of polyols which are useful as poller crosslinkers for use in thermosetting coating compositions, as well as methods of preparation of these materials. In particular, the invention provides crosslinkers of the formula ##STR1## wherein R and R' are independently t-butyl, t-amyl, or phenyl, and x is an integer of from 2 to 5.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: September 16, 1997
    Assignee: Eastman Chemical Company
    Inventors: Philip C. Heidt, Charles H. Foster, J. Stewart Witzeman
  • Patent number: 5527950
    Abstract: The invention relates to a process for the preparation of a 5-formylvalerate ester by hydroformylating a mixture of pentenoate esters in the presence of a catalyst system which catalyst system comprises a metal from group 8-10 of the Periodic Table of Elements and a mono- or multidentate organic phosphorous ligand, wherein the mixture of pentenoate esters contains less than 500 ppm hydroperoxide compounds.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: June 18, 1996
    Assignees: DSM N.V., E.I. Du Pont de Nemours & Co.
    Inventors: Carolina B. Hansen, Antonius J. J. M. Teunissen
  • Patent number: 5466863
    Abstract: Provided are 3-oxoadipate esters of certain polyols which are useful as crosslinkers in thermosetting coating compositions. Also provided are such thermosetting compositions comprised of a curable hydroxyl-functional polymer such as a polyester or acrylic and the crosslinkers of the present invention. Such compositions offer a significant improvement in curing temperature.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: November 14, 1995
    Assignee: Eastman Chemical Company
    Inventors: Philip C. Heidt, Charles H. Foster, J. Stewart Witzeman, Allen L. Crain
  • Patent number: 5412151
    Abstract: Provided are 3-oxoadipate esters of certain polyols which are useful as crosslinkers in thermosetting coating compositions. Also provided are such thermosetting compositions comprised of a curable hydroxyl-functional polymer such as a polyester or acrylic and the crosslinkers of the present invention. Such compositions offer a significant improvement in curing temperature.
    Type: Grant
    Filed: October 22, 1993
    Date of Patent: May 2, 1995
    Assignee: Eastman Chemical Company
    Inventors: Philip C. Heidt, Charles H. Foster, J. Stewart Witzeman, Allen L. Crain
  • Patent number: 5359125
    Abstract: Disclosed are certain novel 2,2'-bisacetoacetates useful as crosslinking agents and a process for the preparation therefor. Also provided are novel enamel compositions containing the crosslinkers and coatings and articles coated with thermosetting coating compositions crosslinked with these novel crosslinkers.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: October 25, 1994
    Assignee: Eastman Chemical Company
    Inventors: J. Stewart Witzeman, Allen L. Crain
  • Patent number: 5260465
    Abstract: This invention relates to pharmaceutical compounds of structural formula (I): ##STR1## and compositions and methods of treatment utilizing these compounds to inhibit farnesyl protein transferase and farnesylation of the oncogene protein Ras.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: November 9, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Sheo B. Singh, Deborah L. Zink
  • Patent number: 5260424
    Abstract: Silylketene acetals, including "living" GTP polymers, are acylated or sulfonylated in the presence of GTP-effective catalysts with acyl or sulfonyl compounds to produce .beta.-ketoesters or .beta.-sulfonylesters; polymeric products, including capped, coupled and chain-extended polymers and block copolymers can be prepared.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: November 9, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Gordon M. Cohen, Hans J. Reich
  • Patent number: 5247122
    Abstract: Disclosed are certain novel 2,2'-bisacetoacetates useful as crosslinking agents and a process for the preparation therefor. Also provided are novel enamel compositions containing the crosslinkers and coatings and articles coated with thermosetting coating compositions crosslinked with these novel crosslinkers.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: September 21, 1993
    Assignee: Eastman Kodak Company
    Inventors: J. Stewart Witzeman, Allen L. Crain, Robert J. Clemens
  • Patent number: 5223621
    Abstract: Transvinylation process between vinyl acetate or vinyl propionate and a carboxylic acid of general formula (I),RCOOH (I)in which R represents a substituted or non-substituted alkyl, cycloalkyl, aralkyl or aromatic radical, in the presence of a palladium catalyst, in which the catalyst is obtained in situ, by reacting, in the reaction medium, a derivative of palladium chosen from the group constituted by palladium II acetate, nitrate or hydroxide and palladium deposited on charcoal, with a tertiary amine chosen from the group constituted by 2,2'-bipyridyl, orthophenanthroline or tetramethylethylenediamine, that the quantity of palladium used, expressed in gram-atom of palladium II per 100 moles of carboxylic acid of general formula (I) is between 0.005 and 1 and that the quantity of amine is greater than 1 and less than 10 moles per gram-atom of palladium II used and use for the preparation of certain products.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: June 29, 1993
    Assignee: Societe Francaise Hoechst
    Inventors: Jean-Claude Vallejos, Yani Christidis
  • Patent number: 5214197
    Abstract: A novel 2,4-dihydroxyadipic acid derivative of the formula: ##STR1## wherein R.sup.1 and R.sup.4 are the same or different and each a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a silyl group, and R.sup.2 and R.sup.3 are the same or different and each a hydrogen atom or a protective group of a hydroxy group or together form a ring, which is useful as a common intermediate in the synthesis of HMG-CoA reductase inhibitor.
    Type: Grant
    Filed: July 2, 1991
    Date of Patent: May 25, 1993
    Assignee: Kanegafuchi Chemical Industry Co., Ltd.
    Inventors: Shigeo Hayashi, Noboru Ueyama, Kenji Inoue, Teruyoshi Koga, Satomi Takahashi
  • Patent number: 5210222
    Abstract: A process, which is harmless with respect to safety, for the production of malonic acid anhydride. For this purpose, diketene is ozonized in the presence of a suitable carbonyl compound. Malonic acid anhydride is a highly reactive intermediate product for the synthesis of numerous active ingredients for, e.g., pharmaceutical agents, pesticides or dyes.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: May 11, 1993
    Assignee: Lonza Ltd.
    Inventor: Colm O'Murchu
  • Patent number: 5206419
    Abstract: Process for the preparation of acetoacetates and other .beta.ketoesters is provided, involving reaction of nitrogen, oxygen or sulfur nucleophiles with a tertiaryalkyl acetoacetate or tertiaryalkyl .beta.-ketoester.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: April 27, 1993
    Assignee: Eastman Kodak Company
    Inventors: J. Stewart Witzeman, W. Dell Nottingham
  • Patent number: 5175300
    Abstract: A process for preparing pyridine-2,3-dicarboxylic acid compounds of the following formula, which comprises preparing .alpha.-halo-oxalacetic acid diesters by reacting oxalacetic acid diester alkali metallic salts with an acid and a halogenating agent or by reacting oxalic acid diesters with halo-acetic acid esters, and then reacting the obtained .alpha.-halo-oxalacetic acid diesters with 2-propenal compounds and ammonia. ##STR1## wherein R.sup.1 and R.sup.2 are, identical or different, a lower alkyl group, and R.sup.3 is a hydrogen atom or a lower alkyl group.The pyridine-2,3-dicarboxylic acid componds obtained by the process of the ivention are useful as an intermediate for manufacturing agricultural chemicals and pharmaceuticals.
    Type: Grant
    Filed: January 9, 1991
    Date of Patent: December 29, 1992
    Assignee: Sugai Chemical Ind. Co., Ltd.
    Inventors: Takaharu Yamashita, Mitsuhiro Kodama
  • Patent number: 5169979
    Abstract: The invention relates to a curing component (A) containing active CH groups, which contains at least two groups of the formula (I) ##STR1## or structural units of the formula (I') or (I") ##STR2## in which: A denotes ##STR3## X and Y are identical or different and denote ##STR4## CO.sub.2 R.sup.1, CN, NO.sub.2, CONH.sub.2, CONR.sup.1 H or CONR.sup.1 R.sup.1, where the R.sup.1 radicals may be identical or different and represent a hydrocarbon radical, preferably an alkyl radical having 1 to 12 carbon atoms, which may also be interrupted by oxygen or an N-alkyl radical, with the proviso that only one of the two radicals X and Y may represent the NO.sub.2 group;A' denotes ##STR5## X' and Y' are identical or different and denote ##STR6## Curable mixtures of (A) and a Michael acceptor (B) and, if appropriate diluents and customary additivies cure rapidly even at low temperatures and are suitable, in particular for surface-coating preparations.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: December 8, 1992
    Assignee: Hoechst AG
    Inventors: Uwe Kubillus, Gerhard Brindopke, Helmut Plum
  • Patent number: 5107015
    Abstract: The preparation of 2-formyl-2-methyl succinates by reacting itaconates with carbon monoxide and hydrogen in contact with a catalyst system comprising rhodium and a tertiary phosphorus compound, wherein the reaction is carried out under a pressure of from 90 to 325 bar.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: April 21, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Bertleff, Gerhard Butz
  • Patent number: 4981973
    Abstract: A process for the transvinylation of a vinyl derivative of a Bronsted acid with a different Bronsted acid which comprises providing a liquid phase mixture containing said vinyl derivative and said Bronsted acid in the presence of a ruthenium compound at a temperature at which transvinylation occurs and recovering as a product of transvinylation the vinyl derivative of the different Bronsted acid. The process is most favorably employed using carboxylic acids to make vinyl esters of carboxylic acids.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: January 1, 1991
    Assignee: Union Carbide Chemicals and Plastics Company, Inc.
    Inventor: Rex E. Murray
  • Patent number: 4902820
    Abstract: Disclosed is a process for the preparation of .alpha.-acyloxycarbonyl compounds by contacting the corresponding .alpha.-dicarbonyl compound with an acyl iodide, which can be employed in an essentially pure form or generated in solution from hydrogen iodide and a carboxylic acid anhydride.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: February 20, 1990
    Assignee: Eastman Kodak Company
    Inventor: Joseph R. Zoeller
  • Patent number: 4849542
    Abstract: A process for the preparation of oxo-alkanedioic acids or diesters thereof by reacting an alkenoic acid or an ester thereof, at least one of the C atoms of the carbon carbon double bond carrying a H atom, with CO and H.sub.2 in the presence of a catalytic system prepared by combining:a. Pd and/or a Pd compound,b. a compound containing an anion of an acid having a pKa of less than 2, except hydrohalogenic acid and carboxylic acids, andc. a bidentate ligandR.sup.1 R.sup.2 --M--R--M--R.sup.3 R.sup.4wherein M is P, As or Sb, R is a divalent organic bridging group having at least two C atoms in the bridge, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are optionally substituted hydrocarbon groups.
    Type: Grant
    Filed: October 28, 1986
    Date of Patent: July 18, 1989
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4800231
    Abstract: Novel keto-diesters are produced by a 2:1 condensation of lower alkyl esters of .alpha.,.beta.-ethylenically unsaturated carboxylic acids and aldehydes having two hydrogen atoms as portions of a formyl group, in the presence of a thiazolium salt as catalyst and a tertiary amine.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: January 24, 1989
    Assignee: Shell Oil Company
    Inventor: Pen C. Wang
  • Patent number: 4644036
    Abstract: Michael addition products of monocarboxylic or dicarboxylic acid esters, capable of undergoing Michael addition, with compounds containing double bonds capable of undergoing Michael addition are suitable for use as a curing component for synthetic resins containing groups capable of amide formation and/or ester formation with carboxylic acids. In particular, the Michael addition products of acetoacetic esters or malonic esters with esters, amides or urea derivatives of .alpha., .beta.-unsaturated monocarboxylic or dicarboxylic acids are used. The structure and the functionality of the curing component can be varied in many ways. It can be attached directly to the synthetic resin molecule, so that self-curing synthetic resins are obtained.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: February 17, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerd Walz, Ernst-August Theiling
  • Patent number: 4600781
    Abstract: The invention relates to 2-formyl-2-halomalonates, and their preparation. The compounds are useful in the preparation of their acetals and also in the preparation of 2-(dicarbethoxymethylene)thiazolidine-4-carboxylic acid.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: July 15, 1986
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Ivan A. Wolff
  • Patent number: 4584145
    Abstract: There is described a process for preparing carbonyl compounds of formula: ##STR1## by oxidation of compounds of formula: ##STR2## wherein X=--CN, --COOR, Y=--COOR.sub.1, --CN, and R, R.sub.1, like or unlike each other, are inert radicals, by employing oxygen or air as oxidants, at least a catalyst selected from the salts of organic or inorganic acids of Mn, Co, Cu and Fe, from 0 to 60 moles of an alkaline salt of an aliphatic carboxylic acid per gram-atom of catalyst metal, in a polar solvent, at temperatures ranging from 30.degree. C. to 200.degree. C. and maintaining the reaction medium anhydrous.The present invention relates to a process for preparing carbonyl compounds by catalytic oxidation of compounds containing an activated methylene group.
    Type: Grant
    Filed: June 19, 1985
    Date of Patent: April 22, 1986
    Assignee: Montedison S.p.A.
    Inventors: Roberto Santi, Giuseppe Cometti, Anselmo Pagani
  • Patent number: 4578503
    Abstract: An alkylated or alkenylated malonic ester having a fluorine containing aliphatic substituent and derivatives thereof as expressed by the following general formula: ##STR1## where R.sub.f is a fluorine containing aliphatic group, R is an aliphatic group, or hydrogen or alkali metal atom, and R' is an unsubstituted or substituted aliphatic group.And a method to trap the enolate ion of a malonic ester having a fluorine containing aliphatic substituent as expressed by the following general formula,R.sub.f CH(CO.sub.2 R).sub.2where R.sub.f is a fluorine containing aliphatic group and R is an aliphatic group, hydrogen or alkali metal atom, wherein said malonic ester is converted under the action of a weaker base and/or fluoride ion to a fluorine containing enolate ion to be trapped as expressed by the following general formula:R.sub.f C.sup..crclbar. (CO.sub.2 R).sub.2where R.sub.f and R are the same as above.
    Type: Grant
    Filed: August 31, 1983
    Date of Patent: March 25, 1986
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Nobuo Ishikawa, Takeshi Nakai, Yoshio Inouye
  • Patent number: 4518793
    Abstract: Disclosed is a process for preparing an acetone dicarboxylic acid diester, which comprises allowing diketene, carbon monoxide and a nitrous acid ester to react in the presence of a palladium halide or a complex thereof.
    Type: Grant
    Filed: October 17, 1983
    Date of Patent: May 21, 1985
    Assignee: UBE Industries, Ltd.
    Inventors: Shinichiro Uchiumi, Kikuo Ataka
  • Patent number: 4401827
    Abstract: Novel acyl-derivatives of the .beta.-hydroxy-.gamma.-butyrobetaine are disclosed (typically pyruvyl carnitine hydrochloride) which are useful therapeutic agents in the treatment of cardiac disorders, hyperlipidoemias and hyperlipoproteinemias.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: August 30, 1983
    Assignee: Sigma-Tau
    Inventor: Paolo de Witt
  • Patent number: 4343953
    Abstract: The present invention relates to a novel method for producing cyclopentenolone of the formula (I), ##STR1## which is a useful intermediate for producing agricultural chemicals, which comprises reacting an acetonedicarboxylic ester of the formula (VII), ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group, with 2-propynyl chloride in the presence of magnesium alkoxide and in the presence of alkali iodide to obtain novel mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI), ##STR3## wherein R is as defined above; hydrolyzing the mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI) under alkaline conditions with an alkali and then reacting the hydrolyzed product with methylglyoxal of the formula, ##STR4## to obtain novel .gamma.-diketone of the formula (V), ##STR5## and ring-closing the .gamma.-diketone of the formula (V) under alkaline condition.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: August 10, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Nobushige Itaya, Kohichi Aketa, Osamu Magara, Toshio Nishioka
  • Patent number: 4338459
    Abstract: A diester of .alpha.-acetyl-.alpha.'-methylsuccinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent mixture containing a non-polar, aprotic liquid, e.g., toluene, and a dipolar aprotic liquid, e.g., DMF, at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt. Further improvement is obtained when the completed reaction mixture is diluted with water and adjusted to pH 8 to 9, and when the DMF/acetoacetate ester ratios are between about 1.7 and 3. The resulting diesters can be used under the conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: July 6, 1982
    Assignee: The Upjohn Company
    Inventor: Francis L. Shenton
  • Patent number: 4324906
    Abstract: A process is disclosed for converting a compound of the formula ##STR1## wherein R and R" are independently methyl, ethyl or propyl;R' is H, Na, Li, K, Mg.sub.1/2, Ca.sub.1/2, Sr.sub.1/2, Ba.sub.1/2, methyl, ethyl or propyl; andQ is chlorine or bromide;directly to a citrate salt by heating in an aqueous medium, with an alkaline earth metal hydroxide, at a temperature greater than 160.degree. C.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: April 13, 1982
    Assignee: Lever Brothers Company
    Inventors: Eddie N. Gutierrez, Vincent Lamberti
  • Patent number: 4311706
    Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: January 19, 1982
    Assignee: INTERx Research Corporation
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4306079
    Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion sequestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.
    Type: Grant
    Filed: September 12, 1979
    Date of Patent: December 15, 1981
    Assignee: Lever Brothers Company
    Inventors: Eddie N. Gutierrez, Vincent Lamberti
  • Patent number: 4304927
    Abstract: Compounds of the structure ##STR1## wherein X is --F or Cl and each R is independently --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 or M where M is an alkali metal, an alkaline earth metal, ammonium or a quaternary ammonium are disclosed. The above compounds are prepared by treating a compound of the structure ##STR2## where each R.sup.1 is independently --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3 or --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ; or ##STR3## with a strong protic acid, followed, as desired, by base hydrolysis to form carboxylate salts (R.dbd.M).
    Type: Grant
    Filed: November 11, 1977
    Date of Patent: December 8, 1981
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4301186
    Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
  • Patent number: 4283553
    Abstract: Disclosed are novel hydroperoxide derivatives of hydroxyethylated compounds of the general formula: ##STR1## a-whole number 10 to 30, b, c are absent, R=n-alkyl from C.sub.8 to C.sub.20, secondary alkyl of C.sub.14, C.sub.15 and ##STR2## where R.sub.2 =n-alkyl from C.sub.8 to C.sub.12 ##STR3## where R.sub.3 and R.sub.4 =R.sub.8 --C.dbd.O, where R.sub.8 =--CH.sub.3 or H, if R.sub.6,7,9 =H R.sub.5 is absent or ##STR4## where R.sub.9 =--CH.sub.3 or H, if R.sub.6,7,8 =H, R.sub.5 is absent; R.sub.10 =n-alkyl of C.sub.1 to C.sub.9 of R.sub.3 .noteq.R.sub.4 R.sub.5 =--CH.sub.2 if R.sub.6,7,8,9 =H; if R.sub.5 is absent, R.sub.1 is acyclic and is ##STR5## R.sub.6 =--CH.sub.3 or H, if R.sub.7,8,9 =H, R.sub.5 is absent, R.sub.7 =--CH.sub.3 or H, if R.sub.6,8,9 =H, R.sub.5 is absent, with x=--O--, b-whole number of 8 to 24, (a+c)-whole number of 6 to 30R=R.sub.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: August 11, 1981
    Inventors: Sergei S. Ivanchev, Anatoly A. Syrov, Valery N. Pavljuchenko, Ninel N. Lesnikova, Diana A. Rozhkova
  • Patent number: 4272442
    Abstract: Novel polyfunctional compounds and a process for their preparation are disclosed. These compounds and their alkali metal salts are useful metal sequestrants and/or detergent builders. Selected compounds are also intermediates useful in the syntheses of aconitic acid as well as isocitric and alloisocitric acids and their lactones. The novel polyfunctional compounds are obtained from the reaction of maleic anhydride with selected active methylene or methine containing compounds.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: June 9, 1981
    Assignee: Lever Brothers Company
    Inventor: Eddie N. Gutierrez
  • Patent number: 4259518
    Abstract: The invention concerns new 3-methyl-5-keto-.alpha.,.omega.-alkene-dioic acids of the general formula ##STR1## wherein the double bond is in one of the positions indicated by the broken lines,R.sub.1 and R.sub.2 independently of one another are a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl group,x is an integer from 9 to 11 andy and z independently of one another are 1 or 2, but cannot both be 1;a process for their preparation and their use for the preparation of macrocyclic .beta.-methyl ketones which are valuable fragrances.
    Type: Grant
    Filed: August 30, 1979
    Date of Patent: March 31, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Bauer, Detlef Hagena
  • Patent number: 4220799
    Abstract: The known condensation reaction of lower alkanoylacetic acid lower alkyl esters with aldehydes catalyzed by amines proceeds safe and in high yields if the amineis an aliphatic tertiary amine. The products are precursors of aromatic amines.
    Type: Grant
    Filed: December 1, 1977
    Date of Patent: September 2, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudiger Berthold, Bernhard Mees, Hartmut Heise
  • Patent number: 4209636
    Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion sequestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.
    Type: Grant
    Filed: May 15, 1978
    Date of Patent: June 24, 1980
    Assignee: Lever Brothers Company
    Inventors: Eddie N. Gutierrez, Vincent Lamberti
  • Patent number: 4194053
    Abstract: A diester of .alpha.-acetyl-.alpha.'-methyl succinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent containing a nonpolar, aprotic liquid at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt having a high surface area (a size of about 60 mesh or smaller). The resulting diesters can also be used under the stabilizing reaction mixture conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.'-methylsuccinate diester with vinyl isobutyl ketone, (or the corresponding Mannich base plus an alkylating agent) and an alkali metal base for a time sufficient to form a reaction mixture containing the .alpha.-methyl-.alpha.'-acetyl-.alpha.
    Type: Grant
    Filed: September 1, 1978
    Date of Patent: March 18, 1980
    Assignee: The Upjohn Company
    Inventor: David R. White
  • Patent number: 4189596
    Abstract: 2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.
    Type: Grant
    Filed: May 2, 1977
    Date of Patent: February 19, 1980
    Assignee: The Upjohn Company
    Inventor: Verlan H. VanRheenen
  • Patent number: 4173707
    Abstract: A cyclopentanol derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 are lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and R.sub.4 is 2-pentenyl or 2-pentynyl, and process for preparing the same.
    Type: Grant
    Filed: June 8, 1978
    Date of Patent: November 6, 1979
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Yuichi Kobayashi
  • Patent number: 4172208
    Abstract: The compound of the formula: ##STR1## is useful as an intermediate to prepare a compound having the generic formula ##STR2## wherein X is selected from groups to provide tetrahydropyran type compounds, 1,4 dioxane type compounds or tetrahydrofuran type compounds, and R is selected from the group consisting of alkali metal, NH.sub.4.sup.+, NH(CH.sub.2 CH.sub.2 OH).sub.3.sup.+, and lower alkyl, branched or straight chain, with up to about C.sub.20 in the chain, useful as a detergent builder.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: October 23, 1979
    Assignee: Monsanto Company
    Inventors: Marvin M. Crutchfield, Kent P. Lannert
  • Patent number: 4146543
    Abstract: Novel polyfunctional compounds and a process for their preparation are disclosed. These compounds and their alkali metal salts are useful metal sequestrants and/or detergent builders. Selected compounds are also intermediates useful in the syntheses of aconitic acid as well as isocitric and alloisocitric acids and their lactones. The novel polyfunctional compounds are obtained from the reaction of maleic anhydride with selected active methylene or methine containing compounds.
    Type: Grant
    Filed: November 4, 1977
    Date of Patent: March 27, 1979
    Assignee: Lever Brothers Company
    Inventor: Eddie N. Gutierrez
  • Patent number: 4123458
    Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion seqestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.
    Type: Grant
    Filed: December 22, 1975
    Date of Patent: October 31, 1978
    Assignee: Lever Brothers Company
    Inventors: Eddie N. Gutierrez, Vincent Lamberti
  • Patent number: 4120874
    Abstract: A compound of the formula ##STR1## wherein R' is lower alkyl, is useful as an intermediate in the preparation of a corresponding tricarboxylate, which is a useful detergent builder.
    Type: Grant
    Filed: January 5, 1977
    Date of Patent: October 17, 1978
    Assignee: Monsanto Company
    Inventors: Marvin M. Crutchfield, Kent P. Lannert