Additional Unsaturation Patents (Class 562/495)
  • Patent number: 4822913
    Abstract: Esters of carboxylic acids of the formula RCH.sub.2 COOR"' and R'CH:C(R")COOR"' are reacted to form a carboxylic acid and an aliphatic alcohol R"'OH wherein R, R', and R" are individually selected from the group consisting of --H, alkyl moieties of from 1 to 18 carbon atoms and aralkyl moieties, cycloalkyl moieties and alkylaryl moieties of 3 to 18 carbon atoms and R"' is an alkyl moiety of 1 to 18 carbon atoms in the presence of an AMS-1B borosilicate crystalline molecular sieve catalyst under reaction conditions.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: April 18, 1989
    Assignee: Amoco Corporation
    Inventor: Gary P. Hagen
  • Patent number: 4806683
    Abstract: A process is disclosed which prepares a cinnamic acid from a cinnamate ester by starting the hydrolysis reaction of the cinnamate ester with an alkali by use of water as a solvent in a heterogeneous binary-phase liquid system to obtain an aqueous alkaline solution of an alkali cinnamate and precipitating the cinnamic acid by conducting an acidifying reaction of said aqueous alkaline solution with a mineral acid so as to keep a pH value of not more than 4 in a resulting liquid.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: February 21, 1989
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Katsuharu Miyata, Usaji Takaki, Toshio Matsuhisa
  • Patent number: 4788330
    Abstract: A polyprenyl compound terminated with a group of ##STR1## is novel and useful as an antihypercholesterolemic agent and an antiarteriosclerotic agent, in which X is a group of the formula ##STR2## (wherein K and L are independently a hydrogen atom or form a single valence bond between the carbon atoms to which they are attached), a group represented by the formula --CH.sub.2 -- or a group represented by the formula --(CH.sub.2).sub.2 --, m is an integer of 0 or 1, and R stands for a hydroxy group, a group represented by the formula ##STR3## wherein R.sup.1 and R.sup.2 may be the same or different and each stands for a hydrogen atom or a lower alkyl group and p stands for an integer of 1 or 2, a group represented by the formula --NH--(CH.sub.2).sub.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: November 29, 1988
    Assignee: Eisai Co., Ltd.
    Inventors: Kouji Nakamoto, Takeshi Suzuki, Shinya Abe, Kenji Hayashi, Akiharu Kajiwara, Isao Yamatsu, Issei Otsuka, Hiroyuki Shiojiri
  • Patent number: 4783549
    Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which --R.sub.1, R.sub.3 and R.sub.4 are each indepenently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 -acyloxy or hydroxyl;--R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;--R" is either a polyene chain or a benzene ring are useful in cosmetics and in the treatment of various dermatological and other complaints.
    Type: Grant
    Filed: September 4, 1985
    Date of Patent: November 8, 1988
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
  • Patent number: 4748273
    Abstract: Amphiphilic diacetylene compound having benzene ring. The compound can readily form a single crystal and is photopolymerizable. A stable monomolecular film or built-up film can be prepared from the diacetylene compound. The film is useful as various electronic materials and optoelectronic materials.
    Type: Grant
    Filed: December 2, 1985
    Date of Patent: May 31, 1988
    Assignee: Kanegafushi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kiyoshige Fukuda, Yasunori Yoshioka, Masakazu Uekita
  • Patent number: 4727181
    Abstract: Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: February 23, 1988
    Assignee: The Dow Chemical Company
    Inventor: William J. Kruper, Jr.
  • Patent number: 4723028
    Abstract: The application discloses certain stilbene compounds, pharmaceutical compositions thereof, method of treating thereof, method of diagnosis therewith, and method for the preparation thereof. The compounds and compositions are useful for diagnosis of leukemia types, the treatment of dermatological disorders, and as differentiation-inducing agents for neoplastic cells.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: February 2, 1988
    Inventor: Koichi Shudo
  • Patent number: 4713486
    Abstract: A compound of formula (I): ##STR1## or a salt, ester or amide thereof, in whichY is a group --O(CH.sub.2).sub.m --, --(CH.sub.2).sub.m -- or --CH.dbd.CH-- where m is an integer of from 1 to 5 n is an integer of from 4 to 14X represents a double or triple bond, and each of A and B represents hydrogen when X is a double bond, or both A and B are absent when X is a triple bond,is useful in the treatment of allergic diseases.
    Type: Grant
    Filed: October 21, 1985
    Date of Patent: December 15, 1987
    Assignee: Beecham Group p.l.c.
    Inventor: Derek R. Buckle
  • Patent number: 4670465
    Abstract: Long chain unsaturated hydrocarbon derivatives, having from 13 to 21 carbon atoms, which are substituted at the 1-position by a phenoxy, phenylthio or a phenyl that bear a carboxylic acid group at the ortho, meta or para positions, and up to 4 carbon-carbon triple bonds, methods of preparing them, and pharmaceutical preparations containing them. These compounds are useful as lipoxygenase inhibitors, and therefore as antiinflammatory agents.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: June 2, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Angel Guzman, Joseph M. Muchowski
  • Patent number: 4613692
    Abstract: A process for the preparation of cinnamic acid is provided by the present invention in which an optionally substituted benzaldehyde and alkali metal salt of carboxylic acid and/or alkali metal (bi) carbonate, as condensing agents, are heated up to a temperature of 100.degree.-220.degree. C. and thereafter there is introduced into the so heated mixture acetic anhydride in at least a stoichiometric amount based upon the amount of optionally substituted benzaldehyde employed. The process can be carried out by heating up a reaction mixture to 100.degree.-220.degree. C. which is free of acetic anhydride or one which contains acetic anhydride but less than a stoichiometric amount thereof based upon the amount of optionally substituted benzaldehyde.
    Type: Grant
    Filed: June 11, 1985
    Date of Patent: September 23, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernhard Beitzke, Volkmar Handschuh, Heinz U. Blank
  • Patent number: 4609756
    Abstract: In the preparation of a cinnamic acid by reacting the corresponding benzaldehyde with ketene in the presence of a catalyst, the improvement which comprises using as the catalyst an iron and/or zinc salt of a mono- or di-carboxylic acid with 2 to 20 carbon atoms containing free carboxylic acid and/or anhydride, and then splitting the reaction product in the temperature range from 100.degree. to 250.degree. C. with an acid or basic catalyst.
    Type: Grant
    Filed: October 4, 1985
    Date of Patent: September 2, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alfons Dorlars, Heinz U. Blank, Herbert Nordt, deceased, Viktor Trescher
  • Patent number: 4599469
    Abstract: Process for the hydrogenation of functionally substituted acetylenic compounds employing catalyst comprising nickel boride on an inorganic oxide support is disclosed. Functionally-substituted acetylenic compounds are selectively reduced under mild reaction conditions to give functionally-substituted cis-olefinic compounds in high yield.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: July 8, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Ted H. Cymbaluk, Jim D. Byers, Marvin M. Johnson
  • Patent number: 4585594
    Abstract: 4-Substituted but-3-ene-1-carboxylic acids and their esters R.sup.1 R.sup.2 C.dbd.CH--CH.sub.2 --CO--O--R.sup.3 (I, where R.sup.1 is an organic radical, R.sup.2 is H or R.sup.1, or R.sup.1 and R.sup.2 together form a 5-membered to 20-membered ring, and R.sup.3 is H or lower alkyl) are prepared by carbonylation of R.sup.1 R.sup.2 C(OH)--CH.dbd.CH.sub.2 (II) in the presence of an alcohol R.sup.3' --OH (III, where R.sup.3' is lower alkyl) or, for the preparation of the acids I alone, in the absence of an alcohol III, at from 50.degree. to 150.degree. C. and under from 200 to 700 bar, using a complex of a palladium halide and a tertiary organic phosphine.
    Type: Grant
    Filed: December 11, 1984
    Date of Patent: April 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Himmele, Werner Hoffmann, Lothar Janitschke
  • Patent number: 4571432
    Abstract: A process for the production of cinnamic acid is disclosed. The process uses an inert diluent to increase the stirrability of the reaction mixture and uses an amine derivative as a catalyst. The present process also uses combinations of acetic acid derivatives to produce the cinnamic acid.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: February 18, 1986
    Assignee: Stauffer Chemical Company
    Inventor: Jeffrey E. Telschow
  • Patent number: 4568764
    Abstract: There is disclosed a process for the production of cinnamic acid wherein different catalysts are used. Suitable catalysts include Lewis acids, transition metal derivatives of acetic acid and halides of alkali metals.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: February 4, 1986
    Assignee: Stauffer Chemical Company
    Inventors: Jeffrey E. Telschow, Edmund J. Rumanowski
  • Patent number: 4557871
    Abstract: Novel styrene derivatives of the general formula ##STR1## wherein X is hydrogen or halogen, X.sup.1 is halogen, R is hydrogen or methyl, Y is hydroxymethyl, carboxyl, --COOR.sup.1 or --COR.sup.2 wherein R.sup.1 is prenyl, geranyl, farnesyl, cyclohexyl, phthalidyl, straight or branched chain alkyl having 1 to 6 carbon atoms, or said alkyl substituted with hydroxy, methoxy, pyridyl or alkanoyloxy having 2 to 16 carbon atoms, and R.sup.2 is amino, hydroxyamino mono-(or di-)alkylamino in which the alkyl moiety contains 1 or 2 carbon atoms, ethoxycarbonylmethylamino, carboxymethylamino, thiazolylamino, cyclohexylamino, pyridylamino, morpholino, N-methylpiperazino, phenylamino, phenylamino substituted with one or two of halogen, hydroxy, methyl, methoxy, trifluoromethyl or carboxyl at the phenyl ring, and the pharmaceutically acceptable salts thereof when Y is carboxyl are disclosed. These compounds exhibit high and long-lasting anti-inflammatory, analgesic and anti-pyretic activity.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: December 10, 1985
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Katsuo Hatayama, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Tomomi Ota, Kazuto Sekiuchi, Kaoru Sota
  • Patent number: 4499300
    Abstract: A multi-step preparation of 4-vinylbenzeneacetic acid from the readily available 1,4-diethylbenzene is described. The method uses cobalt (II) catalyzed oxidation of 1,4-diethylbenzene to 4-ethylacetophenone followed by oxidative rearrangement of the latter to 4-ethylbenzeneacetic acid, selective photochlorination to produce 4-(1'-chloroethyl)benzeneacetic acid, and finally base-catalyzed dehydrochlorination of the latter to afford the title compound.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: February 12, 1985
    Assignee: UOP Inc.
    Inventors: Thomas P. Malloy, Dusan J. Engel
  • Patent number: 4496736
    Abstract: Carboxylic acids and N-t.-alkylamines can be prepared simultaneously by the alkaline pressure hydrolysis of N-t.-alkyl carboxylic acid amides. A 5 to 50% strength by weight aqueous solution of an alkali metal hydroxide is employed for this purpose in an amount of 1.0 to 1.3 mols per mol of the amide. The process is carried out at 200.degree. to 350.degree. C.
    Type: Grant
    Filed: June 3, 1982
    Date of Patent: January 29, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Gerhard Marzolph, Heinz U. Blank
  • Patent number: 4482734
    Abstract: The polyprenyl compound having the formula: ##STR1## wherein X represents a group of the formula: --CH.dbd.CH--, a group of the formula: ##STR2## or a group of the formula: ##STR3## and Y represents a group of the formula: --COOR.sup.1 in which R.sup.1 represents a hydrogen atom or a lower alkyl group or a group of the formula: ##STR4## in which R.sup.2 represents a hydrogen atom or a lower alkyl group, is new and useful as a medicine.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: November 13, 1984
    Assignee: Eisai Co., Ltd.
    Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Yuichi Inai, Yoshikazu Suzuki, Osamu Tagaya
  • Patent number: 4433160
    Abstract: A process for producing an .alpha.-arylalkanoic acid ester represented by the general formula ##STR1## wherein Ar represents an aryl group which may optionally be substituted, and R.sup.1 and R.sup.2, independently from each other, represent a lower alkyl group,which comprises reacting a Grignard reagent prepared from an aryl halide of the general formulaAr--X.sup.1 (II)wherein Ar is as defined above and X.sup.1 represents a halogen atom,and magnesium, with an .alpha.-haloalkanoic acid ester of the general formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and X.sup.2 represents a halogen atom,said reaction of the Grignard reagent with the .alpha.-haloalkanoic acid ester of general formula (III) being carried out in the presence of a nickel compound.
    Type: Grant
    Filed: August 25, 1982
    Date of Patent: February 21, 1984
    Assignee: Taisho Pharmaceutical Company, Ltd.
    Inventors: Takehiro Amano, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Michihiro Ishiguro, Manzo Shiono, Yoshiji Fujita, Takashi Nishida
  • Patent number: 4405810
    Abstract: 7-arylhept-5-ynoic acids and derivatives thereof are anti-allergy and anti-inflammatory agents. As such, they are useful in the treatment of allergy-caused diseases, particularly chronic obstructive lung diseases.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: September 20, 1983
    Assignee: Schering Corporation
    Inventors: David Blythin, Michael J. Green
  • Patent number: 4390476
    Abstract: Phosphonium compounds of the formula(R).sub.3 P.sup..sym. --CH.sub.2 --X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar.in which R is preferably alkyl having 1 to 4 C atoms, cyclohexyl or phenyl, R.sub.1 is a substituted or unsubstituted aromatic radical, especially a phenyl radical, X is phenylene, 4,4'-biphenylene or 1,4- or 2,6-naphthylene and Y.sup..crclbar. is SO.sub.3.sup..crclbar., SO.sub.2.sup..crclbar. or COO.sup..crclbar., a process for their preparation and a process for the preparation of asymetrically substituted fluorescent brightening agents of the formulaZ--CH.dbd.CH--X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar. M.sup..sym.in which R.sub.1, X and Y.sup..crclbar. are as defined above, M.sup..sym. is a cation and Z is preferably a substituted or unsubstituted phenyl or 2-phenyl-triazol-4-yl radical, by reacting a bis-phosphonium compound of the formula ##STR1## in which Q.sup..crclbar. is an anion, with an aldehyde of the formula M.sup..sym. Y.sup..crclbar. --R.sub.
    Type: Grant
    Filed: November 5, 1981
    Date of Patent: June 28, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Michael Marky
  • Patent number: 4362891
    Abstract: An alkanoic acid compound is disclosed of formula: ##STR1## and certain of its physiologically acceptable salts and esters. The alkanoic acid compound and its salts and esters have an unexpectedly greater anti-inflammatory activity than representative members of a broad class of compounds, phenyl alkane derivatives, known to have therapeutic properties. The alkanoic acid compound also has unexpectedly high antipyretic and analgesic activity. The compounds may be formulated in conventional manner as pharmaceutical compositions.The compound may be prepared from 2-[4-(1-hydroxy-2-dimethylethyl)phenyl] propionic acid directly by dehydration or via an ester by dehydration in the presence of an alkanol followed by hydrolysis.
    Type: Grant
    Filed: June 17, 1980
    Date of Patent: December 7, 1982
    Assignee: Glaxo Group Limited
    Inventors: Alfredo Guerrato, Michele Perchinunno
  • Patent number: 4355168
    Abstract: There is disclosed and claimed a process for preparing aryl- and heteroarylhexadienoic acids which is characterized in that an aryl- or heteroarylacetylene having the formula: R--C.tbd.CH, wherein R is an aryl or heteroaryl group, optionally substituted and having in the aggregate up to 20 carbon atoms, is reacted with 3-butenoic acid CH.sub.2 .dbd.CH--CH.sub.2 --COOH, in an alcoholic medium, at temperatures maintained between 50.degree. C. and 120.degree. C., approximately, in the presence of a catalyst selected from among the phosphinic complexes of rhodium having the formulas: III, Rh(PR'.sub.3).sub.n L.sub.m X associated with alkaline salts of carboxylic acids having up to 4 carbon atoms, and IV, Rh(PR'.sub.3).sub.n L.sub.p.sup.+ Y.sup.
    Type: Grant
    Filed: December 2, 1980
    Date of Patent: October 19, 1982
    Assignee: Montedison S.p.A.
    Inventors: Gian P. Chiusoli, William Giroldini, Luciano Pallini, Giuseppe Salerno
  • Patent number: 4347379
    Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: August 31, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4324796
    Abstract: Substituted oxiranecarboxylic acids of the formula ##STR1## wherein R.sup.1 denotes a hydrogen atom (--H), a halogen atom, a hydroxyl roup, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group,R.sup.2 has one of the meanings of R.sup.1,R.sup.3 denotes a hydrogen atom (--H) or a lower alkyl group andn denotes an integer from 1 to 5, andthe salts of the acids are new compounds. They display a hypoglycaemic action in warm-blooded animals. Processes for the preparation of the new compounds and of the intermediate products required for their preparation are described.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: April 13, 1982
    Assignee: BYK Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung
    Inventors: Klaus Eistetter, Erich Rapp
  • Patent number: 4316860
    Abstract: Phosphonium compounds of the formula(R).sub.3 P.sup..sym. --CH.sub.2 --X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar.in which R is preferably alkyl having 1 to 4 C atoms, cyclohexyl or phenyl, R.sub.1 is a substituted or unsubstituted aromatic radical, especially a phenyl radical, X is phenylene, 4,4'-biphenylene or 1,4- or 2,6-naphthylene and Y.sup..crclbar. is SO.sub.3.sup..crclbar., SO.sub.2.sup..crclbar. or COO.sup..crclbar., a process for their preparation and a process for the preparation of asymetrically substituted fluorescent brightening agents of the formulaZ--CH.dbd.CH--X--CH.dbd.CH--R.sub.1 Y.sup..crclbar. M.sup..sym.in which R.sub.1, X and Y.sup..crclbar. are as defined above, M.sup.61 is a cation and Z is preferably a substituted or unsubstituted phenyl or 2-phenyl-triazol-4-yl radical, by reacting a bis-phosphonium compound of the formula ##STR1## in which Q.sup..crclbar. is an anion, with an aldehyde of the formula M.sup..sym. Y.sup..crclbar. --R.sub.
    Type: Grant
    Filed: May 15, 1980
    Date of Patent: February 23, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Michael Marky
  • Patent number: 4309357
    Abstract: Dienoic acids are prepared by reaction of salts of 3-butenoic acid and vinyl halides, in the presence of catalysts which are phosphinic complexes of rhodium or nickel.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: January 5, 1982
    Assignee: Montedison S.p.A.
    Inventors: Gian P. Chiusoli, William Giroldini, Giuseppe Salerno
  • Patent number: 4307034
    Abstract: An inert organic solvent dispersion of alkali hydroxide is prepared by mixing an alkali hydroxide, an inert organic solvent and a stabilizer and heating and stirring at the temperature for forming the pasty alkali hydroxide and cooling the dispersion. The dispersion of alkali hydroxide is used in a reaction of an active methylene compound with an organoalkyl halide such as a reaction of a halophenylacetonitrile with an isopropyl halide to obtain .alpha.-isopropyl halophenylacetonitrile.
    Type: Grant
    Filed: September 13, 1979
    Date of Patent: December 22, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
  • Patent number: 4307232
    Abstract: Process for preparing the substituted phosphonoalkanoic acid of the formula ##STR1## wherein: R.sup.1 is alkyl of 1-8 carbon atoms, aralkyl of 7-10 carbon atoms, phenyl, or substituted phenyl of 6-10 carbon atoms;R.sup.2 is H, hydrocarbyl of 1-18 carbon atoms, or substituted hydrocarbyl of 1-18 carbon atoms, wherein in said hydrocarbyl groups the carbon atom attached to the ##STR2## moiety is substituted with two or three hydrogen atoms or is a carbon atom of an aromatic ring; andY is oxygen or sulfur,which process comprises contacting and reacting, at a temperature of about -70.degree. C. to about 125.degree. C., a pressure of about 1-100 atmospheres (0.1-10 MPa), and for a time sufficient to effect reaction, the phosphite ester of the formula ##STR3## wherein R.sup.1 and Y are as defined above, with the .alpha.-halocarboxylic acid of the formula R.sup.2 CHXCO.sub.2 H, wherein X is Cl, Br, or I and R.sup.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: December 22, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David R. Brittelli
  • 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: 4284832
    Abstract: Tear gas or CS (o-Chlorobenzalmalononitrile) has two nitrile functional gps which, when removed, effects the chemical conversion of bulk CS to o-chlorostyrene. This involves a first step, an acid or base catalyzed hydrolysis of CS to o-chlorocinnamic acid. Thereafter a second reaction is the decarboxylation of the intermediate product to give o-chlorostyrene.CS is reacted with 70% sulfuric acid at 120.degree. C., producing ammonium sulfate and orth-ochlorocinnamic acid (the intermediate product). This intermediate product is separated and thermally decarboxylated at 270.degree. C. (with a catalytic amount of soda lime and copper powder) to ortho-chlorostyrene.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: August 18, 1981
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Solim S. W. Kwak
  • Patent number: 4255313
    Abstract: The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4',4'-benzophenonetetracarboxylic acid, an aromatic diamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 20, 1979
    Date of Patent: March 10, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Patricia A. Antonoplos, William J. Heilman
  • Patent number: 4251417
    Abstract: The products of the invention are acetylene end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3',4,4' benzophenonetetracarboxylic acid, an aromatic triamine, and an acetylene-substituted aromatic monoamine. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Wai Y. Chow, William J. Heilman
  • Patent number: 4251543
    Abstract: 2-(p-prenylphenyl)propionic acid and pharmaceutically acceptable salts thereof are disclosed. They exhibit anti-inflammatory and analgesic activity with low gastrointestinal action.
    Type: Grant
    Filed: June 4, 1979
    Date of Patent: February 17, 1981
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Takehiro Amano, Jiro Sawada, Michitada Sasajima
  • Patent number: 4251420
    Abstract: The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid, an aromatic triamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Patricia A. Antonoplos, William J. Heilman
  • Patent number: 4251419
    Abstract: The products of the invention are vinyl end-capped oligomers which have the structure as shown in FIG. 3. The products are prepared from either of two (2) precursors. The first precursor is a compound which has the structure as shown in FIG. 2. The second precursor is a complex amine salt which has the structure shown in FIG. 5.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: William J. Heilman, Daniel J. Hurley
  • Patent number: 4207266
    Abstract: This invention relates to a novel process for the direct trifluoromethylation of aromatic compounds via carbon tetrachloride and hydrogen fluoride in the presence of strong Bronsted or Lewis acids which give an acidic reaction (increase in concentration of H.sub.2 F.sup.+ ions) in anhydrous hydrogen fluoride.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: June 10, 1980
    Assignee: Rohm and Haas Company
    Inventor: Thomas R. Opie
  • Patent number: 4204071
    Abstract: Benzyl esters and thiolesters of 4-aryl-3-butenoic acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters for the control of pests.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: May 20, 1980
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4166131
    Abstract: This invention provides new compounds of formula I, ##STR1## wherein R.sub.1 is lower alkyl,R.sub.2 is hydrogen or lower alkyl,R.sub.3 is hydrogen or lower alkyl,R.sub.4 is hydrogen or lower alkyl,R.sub.5 is hydrogen, chlorine or lower alkyl, and each ofR.sub.6 and R.sub.7 is hydrogen, or, when R.sub.5 is hydrogen, R.sub.6 may also be chlorine or lower alkyl, and R.sub.7 chlorine or lower alkyl,Useful as anti-phlogistic and anti-arthritic agents.
    Type: Grant
    Filed: October 24, 1974
    Date of Patent: August 28, 1979
    Assignee: Hexachimie Societe Anonyme
    Inventor: Trevor G. Payne
  • Patent number: 4161535
    Abstract: 2-Isopropyl-4-phenyl-3-butenoic acid benzyl esters of the formula ##STR1## wherein Y is hydrogen, halogen or methyl. Processes for producing them, and their use in combating pests.
    Type: Grant
    Filed: September 26, 1977
    Date of Patent: July 17, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Jozef Drabek, Saleem Farooq, Laurenz Gsell, Odd Kristiansen
  • Patent number: 4145362
    Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: March 20, 1979
    Assignee: S.A. P R B en Neerlandais PRB N.V.
    Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem