Aromatic Alcohol Moiety Patents (Class 560/254)
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Patent number: 4857572Abstract: Novel compositions are described which contain an elastomer or a tackifying resin and at least one compound of formula I ##STR1## The symbols R.sub.1 is alkyl or cycloalkyl, R.sub.2 is alkyl, hydroxyalkyl, phenyl or benzyl, and R.sub.3 is hydrogen or methyl with the proviso that, when R.sub.1 is other than methyl, R.sub.3 is methyl.Type: GrantFiled: February 10, 1988Date of Patent: August 15, 1989Assignee: Ciba-Geigy CorporationInventors: Hans-Rudolf Meier, Gerrit Knobloch
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Patent number: 4820823Abstract: In accordance with a process of the present invention, .alpha.-keto acids of the general formula RCOCOOH wherein R is aryl, alkenyl or heterocyclic group, can be obtained through one-step carbonylation reaction of an organic halogenide of the general formula RX wherein R is the same as above and X is a halogen atom, with carbon monoxide and water in the presence of a basic compound and a palladium containing catalyst.Type: GrantFiled: February 21, 1986Date of Patent: April 11, 1989Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Masato Tanaka, Toshiaki Kobayashi, Toshiyasu Sakakura
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Patent number: 4785004Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted by one or more halogen atoms having an atomic number of at most 17,R.sup.2 represents an aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene, a single bond or vinylene,B.sup.1 represents C.sub.1-7 -alkylene or phenylene,B.sup.2 represents a single bond, ethylene or phenylene, andM represents an aromatic radical of the partial formula ##STR2## in which the symbols have the following meanings: R.sup.3 represents hydrogen or C.sub.1-4 -alkyl,X represents NH, O, S or if R.sup.4 represents hydrogen, a single bond,one of the symbols R.sup.4 and R.sup.5 represents hydrogen and the other represents the group --CO--R.sup.6, orR.sup.4 and R.sup.5 together represent the radical --CO--C(R.sup.6).dbd.C(R.sup.7)--or--CO--C(R.sup.7).dbd.C(R.sup.6)--orR.sup.4 R.sup.Type: GrantFiled: December 15, 1986Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventors: Andreas Von Sprecher, Werner Breitenstein, Andreas Beck, Robert W. Lang, Konrad Oertle
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Patent number: 4780542Abstract: The invention relates to the preparation of an ester or an amide from an anhydride with an alcohol or an amine, wherein the anhydride is first prepared by reacting an acid and an alkyl chloroformate in a 100% aqueous medium, that is, 100% water.Type: GrantFiled: September 26, 1983Date of Patent: October 25, 1988Assignee: Montefiore Medical CenterInventor: Iraj Lalezari
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Patent number: 4721805Abstract: A process is provided for making acyloxy benzene sulfonates by the steps of sulfonating with SO.sub.3, digesting the sulfonation adduct, and neutralizing. The sulfonation adduct can spontaneously rearrange. Unless the rearrangement is controlled as taught in the sulfonating and digesting steps, product yields of acyloxy benzene sulfonate drop to unusable levels and the color of the product is poor and the content of by-products is excessive in the product.Type: GrantFiled: November 28, 1986Date of Patent: January 26, 1988Assignee: Stepan CompanyInventor: Marvin Nussbaum
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Patent number: 4709081Abstract: The invention relates to a process for the preparation of compounds of formula (I) ##STR1## wherein R.sup.1 stands for hydrogen or the group COR.sup.2, whereinR.sup.2 stands for a straight or branched chained alkyl having 1 to 8 carbon atoms optionally substituted with phenyl, naphthyl, tetrahydronaphthyl or m-phenoxy-benzyl, cycloalkyl having 3 to 6 carbon atoms optionally substituted with one or more straight or branched chained alkyl or alkenyl having 1 to 6 carbon atoms, phenyl or naphthyl.The compounds of formula (I) are prepared according to the invention by(a) reacting esters of formula (II) ##STR2## wherein X stands for chlorine or bromine andR.sup.2 has the same meanings as defined above with a phenol alkali metal salt and(b) if desired converting the diphenyl ethers so obtained to a specific compound of formula (I), m-phenoxybenzyl alcohol by the hydrolysis of the ester group.Type: GrantFiled: September 26, 1985Date of Patent: November 24, 1987Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Gergely Heja, Dezso Korbonits, Endre Palosi, Pal Kiss, Csaba Gonczi, Ida Szvoboda nee Kanzel, Ede Marvanyos, Judit Kun, Maria Szomor nee Wundele, Gabor Szabo, Tamas Kallay, Laszlo Ledniczky
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Patent number: 4670581Abstract: New biphenyl compounds and a process for producing them are provided. These new compounds have an acyloxy group in the 2- or 4-position of the biphenyl and an acyl hydroxyalkyl, hydroxyalkenyl or vinyl group in the 4'-position of the biphenyl or, alternatively a hydroxyl group in the 2- or 4-position of the biphenyl and an acyl, hydroxyalkyl, hydroxyalkenyl or vinyl group in the 4'-position of the biphenyl. These compounds can be produced easily from 2- or 4-acyloxybiphenyl compounds.Type: GrantFiled: January 10, 1984Date of Patent: June 2, 1987Assignee: Sugai Chemical Industry Co., Ltd.Inventor: Teiichi Tanigaki
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Patent number: 4665223Abstract: A process for the production of 1-alkoxyalkyl esters comprises reacting an unsaturated ester with an alcohol in the presence of a Lewis base containing catalyst. The Lewis base containing catalyst is preferably (i) an amidine, or (ii) a Lewis base and an epoxide or (iii) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne. The process can be used to prepare, for example, 1-methoxyethyl acetate from vinyl acetate and methanol under mild conditions.Type: GrantFiled: January 15, 1985Date of Patent: May 12, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4661601Abstract: New compounds having the formula 1 ##STR1## wherein W is hydrogen, halogen, n-alkyl, --NHCOR.sup.1, --COR.sup.1, or phenoxyacetylamino optionally substituted by one or two C.sub.1-12 straight- or branched chain alkyl, X is a substituent in the coupling position and is selected from hydrogen, chlorine, bromine, --SR.sup.11 or a nitrogen-containing heterocyclic residue attached at a ring nitrogen atom, and Y is a group having the formula 2 ##STR2## wherein Q is selected from the residues: --COOR.sup.4 or --CONR.sup.4 R.sup.5, --OM, --NR.sup.7 R.sup.8, --PO(OR.sup.9)[O].sub.x R.sup.10 with X=0 or 1, --SO.sub.2 OH, --SO.sub.2 NR.sup.4 R.sup.5 or CN. The groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, M, k and n are defined hereinafter.These compounds are used as black color couplers in photographic materials.Type: GrantFiled: April 3, 1985Date of Patent: April 28, 1987Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4650898Abstract: Described are 2-methyl-4-phenyl-1-pentanol derivatives defined according to the structure: ##STR1## wherein R represents hydrogen or acetyl and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, medicinal products and chewing tobaccos.Type: GrantFiled: December 14, 1984Date of Patent: March 17, 1987Assignee: International Flavors & Fragrances Inc.Inventor: John B. Hall
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Patent number: 4623749Abstract: Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide with a substituted or unsubstituted prenyl ester having the structure: ##STR2## wherein R.sub.3 represents C.sub.1 -C.sub.Type: GrantFiled: August 17, 1984Date of Patent: November 18, 1986Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Gilbert Stork, Braja D. Mookherjee, Howard H. Heinsohn, Jr.
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Patent number: 4616082Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.Type: GrantFiled: June 7, 1985Date of Patent: October 7, 1986Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4613457Abstract: Methyl pentanoic acid esters corresponding to the formula ##STR1## wherein R is an olefinically unsaturated, straight-chain or branched-chain or carbocyclic hydrocarbon group, a phenyl or alkyl substituted phenyl group, a phenyl substituted alkyl group, or a phenyl substituted alkenyl group, wherein R contains from 3 to 9 carbon atoms, are valuable perfumes having strong, generally vegetably odor notes and outstanding persistence. They are produced by esterifying 2-methyl pentanoic acid with an unsaturated or carbocyclic alcohol or phenol containing radicals R corresponding to the general formula.The compounds can be effectively combined with other perfumes and standard perfume ingredients to form new compositions. The methyl pentanoic acid ester content thereof generally amounts to between about 1 and about 50% by weight.Type: GrantFiled: February 9, 1984Date of Patent: September 23, 1986Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Siegfried Blosl, Klaus Bruns, Ulf-Armin Schaper
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Patent number: 4610812Abstract: Described are 2-methyl-4-phenyl-1-pentanol derivatives defined according to the structure: ##STR1## wherein R represents hydrogen or acetyl and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, medicinal products and chewing tobaccos.Type: GrantFiled: October 4, 1985Date of Patent: September 9, 1986Assignee: International Flavors & Fragrances Inc.Inventor: John B. Hall
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Patent number: 4603208Abstract: Novel polyprenyl compounds have the general formula: ##STR1## represents a cis-isoprene unit, n is an integer of 11-19, Z.sup.1 is --CH.sub.2 OH or a functional precursor thereof, and either one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is --S(O).sub.m R.sup.3 in which m is an integer of 0 (zero), 1 or 2 and R.sup.3 is a phenyl, naphthyl, pyridyl or thiazolinyl group or such group substituted with at least one lower alkyl and/or halogen substituent. The topic novel polyprenyl compounds can be synthesized from derivatives of the polyprenol which is obtainable from leaves of Ginkgo biloba or Cedrus deodara, among others, by extraction, if necessary followed by hydrolytic treatment. The novel polyprenyl compounds can be converted to mammalian dolichols or precursors thereof by reductive elimination of the --S(O).sub.m R.sup.3 group.Type: GrantFiled: February 10, 1983Date of Patent: July 29, 1986Assignee: Kuraray Co., Ltd.Inventors: Takashi Onishi, Shigeaki Suzuki, Fumio Mori, Tetsuo Takigawa, Yoshiji Fujita, Masao Mizuno, Takashi Nishida
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Patent number: 4593029Abstract: Novel compound of the formula ##STR1## wherein n is an integer of 1 to 8;R.sub.1 is hydrogen or alkyl of 1-6 carbons;R.sub.2 is hydrogen;R.sub.3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoyl alkyl, carboxyalkyl, alkoxycarbonylalkyl;R.sub.4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl;Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy;any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.These compounds are inhibitors of thromboxane synthetase and cyclic AMP phosphodiesterase and are therefore potential cardiovascular agents particularly useful as platelet aggregation inhibitors and anti-thrombotic agents. Accordingly, these compounds will preferably be useful in treating cardiovascular disorders with thrombotic complications. However, they also possess vasodilatory, antisecretory, antihypertensive, inotropic and antimetastatic activities.Type: GrantFiled: February 15, 1984Date of Patent: June 3, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Michael C. Venuti, John J. Bruno
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Patent number: 4588835Abstract: A process for preparing an alkoxyphenol represented by the formula: ##STR1## wherein R is hydrogen, alkyl having 1 to 4 carbon atoms, formyl, hydroxymethyl, alkoxymethyl, dialkoxymethyl, acetoxymethyl or diacetoxymethyl, R' is alkyl having 1 to 4 carbon atoms, and n is an integer of 1 to 5, characterized in that a phenol halide represented by the formula: ##STR2## wherein R and n are as defined above, and X is chlorine or bromine is reacted, in the presence of a copper salt serving as a catalyst and of a solvent, with a product prepared by heating, in the presence of a dehydrating agent, an alkali metal hydroxide and a compound of the formula R'OH wherein R' is as defined above.Type: GrantFiled: October 19, 1984Date of Patent: May 13, 1986Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Mitsuo Akada
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Patent number: 4587366Abstract: A process is described for preparing fluoroalkyl-substituted iodoalkanes by reacting a fluorinated alkyl iodide with a substituted or unsubstituted alkene under heat in the presence of a catalyst. The catalyst is at least one metal which, in the periodic table of the elements, has one of the atomic numbers 24 to 30, 42 to 48 or 74 to 79 and is in finely divided form. The products of the process according to the invention are addition compounds of the fluorinated alkyl iodide with the substituted or unsubstituted alkene and, in known processes, can be used as useful intermediates for preparing fluorine-containing polymers, textile finishes, fire-extinguishing agents or surfactants.Type: GrantFiled: October 19, 1984Date of Patent: May 6, 1986Assignee: Hoechst AktiengesellschaftInventor: Konrad von Werner
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Patent number: 4560791Abstract: Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.Type: GrantFiled: November 14, 1983Date of Patent: December 24, 1985Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Gilbert Stork, Braja D. Mookherjee, Howard H. Heinsohn, Jr.
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Patent number: 4559177Abstract: A compound of the formula: ##STR1## wherein m is an integer of 11 to 22; R.sub.1 is alkyl having 1 to 4 carbon atoms; R.sub.2 is hydrogen, alkyl having 1 to 4 carbon atoms or carboxylic acyl having 1 to 8 carbon atoms. Such compounds have pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory and lysosomal membrane stabilizing activity, and inhibit SRS-A production, and are useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.Type: GrantFiled: June 30, 1980Date of Patent: December 17, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Tetsuya Okutani, Giichi Goto
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Patent number: 4559179Abstract: A fluorine-containing vinyl compound of the formula: ##STR1## wherein Rf is fluoroalkyl of 4 to 20 carbon atoms, R.sub.1 is hydrogen or acyl of 1 to 3 carbon atoms, one of R.sub.2 and R.sub.3 is hydrogen and the other is methyl, R.sub.4 is hydrogen or methyl, A is a divalent organic group, and l, m and n are each an integer of 0 to 40 and satisfy 0<l+m+n.ltoreq.40, which can modify surface properties of resins.Type: GrantFiled: April 5, 1984Date of Patent: December 17, 1985Assignee: Daikan Kogyo Co., Ltd.Inventors: Iwao Hisamoto, Chiaki Maeda, Masaru Hirai
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Patent number: 4535182Abstract: 2-Cyclopentenone esters of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is lower alkyl, lower alkenyl, lower alkynyl, or cycloalkyl, cycloalkenyl or substituted or unsubstituted aryl and R.sup.3 is hydrogen or lower alkyl are prepared in high yields by reacting the corresponding racemic or optically active 4-cyclopentenone of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above and R.sup.3 is hydrogen or acyl with at least one lower aliphatic carboxylic acid and/or metal or amine salts thereof.Type: GrantFiled: August 16, 1983Date of Patent: August 13, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Tadashi Katsura
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Patent number: 4499272Abstract: 2-Hydroxy-3-halo-1-propanesulfonates are reacted with certain arylamines, preferably in the presence of a base such as KOH or NaOH in one or more of ethylene glycol, propylene glycol, 2-ethoxyethanol and the like to give 2-hydroxy-3-(arylamino)-1-propanesulfonates useful as couplers for acid dyes for polyamide fibers. The present coupler products which are derivatives of aniline, tetrahydroquinoline, and benzomorpholine, have the general formulae ##STR1## wherein the rings may be substituted with a wide variety of substituents known to the dye art;M is NH.sub.4.sup.+ or a group IA metal, preferably Na.sup.+, or K.sup.+ ; andR.sup.3 is hydrogen or a group such as alkyl, cycloalkyl and aryl, each of which may be substituted.Type: GrantFiled: August 20, 1982Date of Patent: February 12, 1985Assignee: Eastman Kodak CompanyInventors: John A. Hyatt, Clarence A. Coates, Jr.
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Patent number: 4499298Abstract: A process is described for the preparation of aryl esters such as benzyl acetate by reacting an aryl alkyl compound such as toluene with a carboxylic acid such as acetic acid and oxygen in the presence of a catalytically effective amount of a catalyst comprising palladium metal, gold metal and a metal of Group VA of the Periodic Table of the Elements such as bismuth.Type: GrantFiled: December 20, 1979Date of Patent: February 12, 1985Assignee: National Distillers and Chemical CorporationInventors: John A. Scheben, James A. Hinnenkamp
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Patent number: 4496767Abstract: A novel process for preparing 2-cyclopentenones of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl and R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: ##STR4## wherein R.sub.1 and R.sub.2 are each as defined above and R is hydrogen or C.sub.1 -C.sub.4 alkyl and subjecting the resulting mixture to reduction.Type: GrantFiled: October 18, 1983Date of Patent: January 29, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Tadashi Katsura
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Patent number: 4495104Abstract: A compound of the general formula ##STR1## wherein n is an integer of 10 to 21, inclusive; R is H or lower alkyl having 1 to 4 carbon atoms has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory, lysosomal membrane stabilizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.Type: GrantFiled: July 11, 1980Date of Patent: January 22, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Isuke Imada, Tetsuya Okutani, Masazumi Watanabe
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Patent number: 4481148Abstract: Hydroxyl-containing liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one of selected vinylidene monomers having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) at least one hydroxyl-containing disulfide in the presence of (3) ultraviolet radiation.Type: GrantFiled: March 16, 1981Date of Patent: November 6, 1984Assignee: The B. F. Goodrich CompanyInventor: Changkiu K. Riew
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Patent number: 4477681Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, chlorine, phenyl, dialkylamino of 2-4 carbon atoms or alkyl or alkoxy each of up to 18 carbon atoms; R.sub.2 is hydrogen, chlorine, bromine or alkyl or alkoxy each of up to 4 carbon atoms; R.sub.3 and R.sub.4, which can be the same or different, each is hydrogen or alkyl of up to 6 carbon atoms; R.sub.5 is hydrogen or alkyl or alkanoyl each of up to 4 carbon atoms; and R.sub.6 is hydrogen or methyl, with the proviso that not all of R.sub.1 to R.sub.6 simultaneously are hydrogen, are effective photosensitizers, especially for photopolymerization of unsaturated compounds and for hardening of printing dyes.Type: GrantFiled: August 16, 1982Date of Patent: October 16, 1984Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Juergen Gehlhaus, Manfred Kieser
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Patent number: 4469703Abstract: The invention relates to nitroalkanol derivatives of the general formula (I), ##STR1## wherein R.sub.1 is a C.sub.2-12 alkenyl or alkadienyl group, a C.sub.4-12 alkoxyalkyl or alkoxyalkenyl group having one or more C.sub.1-3 alkyl substituents, a C.sub.3-6 cycloalkyl or cycloalkenyl group, a furyl group, a nitrofuryl group, or a phenyl group having optionally one or more identical or different substituents selected from the group consisting of hydroxy, C.sub.1-4 alkoxy, halogen, nitro, C.sub.1-4 alkylenedioxy and C.sub.1-4 alkenoyloxy groups,R.sub.2 and R.sub.4 each represent hydrogen or they form together a valence bond,R.sub.3 is a C.sub.1-12 alkanoyloxy group, a benzoyloxy group having optionally one or more halogen substituents or hydrogen atom, andR.sub.5 is a C.sub.1-12 alkyl group or a phenyl group having optionally one or more halogen substituents,with the proviso that if R.sub.2 and R.sub.4 each stand for hydrogen, R.sub.1 is other than unsubstituted phenyl and R.sub.3 may represent only a C.sub.Type: GrantFiled: February 22, 1982Date of Patent: September 4, 1984Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Attila Kis-Tamas, Gyula Mikite, Erzsebet Csutak nee Jakucs, Laszlo Kocsis
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Patent number: 4443625Abstract: The present invention relates to crop culture and is particularly concerned with practices for conserving soil nitrogen and for supplying the soil nitrogen requirements for plant nutrition. These practices involve the employment, as active agent, of a novel butane compound having the formula ##STR1## wherein X is H or ##STR2## R is H or C.sub.1 -C.sub.8 alkyl; R' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo and n is an integer from 0 to 2.Type: GrantFiled: May 14, 1981Date of Patent: April 17, 1984Assignee: The Dow Chemical Co.Inventors: Jeffrey D. Griffith, Thomas M. Ozretich
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Patent number: 4433159Abstract: Optically active alpha-tocopherol is synthesized by a multi-step process using phytol as a starting material. The process does not require an optical resolution step.Type: GrantFiled: February 18, 1982Date of Patent: February 21, 1984Assignee: Eisai Co., Ltd.Inventors: Kimio Hamamura, Kozo Akasaka, Youji Yamagishi
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Patent number: 4431835Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) chromium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 14, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4430506Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) vanadium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 7, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4421739Abstract: The invention provides compounds which are particularly valuable for use as the active ingredient in sun tan lotions and creams and the like. These compounds have the general formula: ##STR1## in which Y denotes hydrogen or the radical SO.sub.3 H or a salt thereof with an organic or inorganic base, and Z denotes the radical --CH.sub.2 Br or --CHBrBr or a radical Z' which denotes the radical --CH.sub.2 I, --CH.sub.2 R, --CHR'R', --CHO or --COOR", in which R denotes --NR.sub.1 R.sub.2, --N.sup.+ R.sub.1 R.sub.2 R.sub.3, --OR.sub.4, --OCOR.sub.5, --SR.sub.6, --CN, -COOR" or --SSO.sub.3 Na, in which R.sub.1 and R.sub.2 independently denote hydrogen, C.sub.1-18 alkyl or hydroxyalkyl, or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, denote a heterocyclic ring, R.sub.3 denotes C.sub.1-4 alkyl or hydroxyalkyl or sulphonatopropyl, R.sub.4 denotes hydrogen, alkyl, polyoxyethylene, aryl which is optionally substituted, menthyl or dialkylaminoalkyl, R.sub.Type: GrantFiled: March 14, 1978Date of Patent: December 20, 1983Assignee: L'OrealInventors: Claude Bouillon, Charles Vayssie
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Patent number: 4410734Abstract: S-Configurated phenylpropane derivatives of the formula ##STR1## where R.sup.1 is alkyl, aryl or alkoxy, R.sup.2 is hydrogen, alkyl, aryl or alkoxy, and R.sup.3 is carboxyl or esterified carboxyl, acetalized formyl, hydroxymethyl or esterified hydroxymethyl, their preparation by microbiological hydrogenation, and their use for the preparation of fungicidal compounds.Type: GrantFiled: December 8, 1980Date of Patent: October 18, 1983Assignee: BASF AktiengesellschaftInventors: Christoph Martin, Walter Himmele, Hardo Siegel
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Patent number: 4407757Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.Type: GrantFiled: December 31, 1980Date of Patent: October 4, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
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Patent number: 4407760Abstract: A method for the preparation of difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent mixture.Type: GrantFiled: September 20, 1982Date of Patent: October 4, 1983Assignee: American Cyanamid CompanyInventor: Jack K. Siddens
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Patent number: 4405529Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.Type: GrantFiled: September 20, 1982Date of Patent: September 20, 1983Assignee: American Cyanamid CompanyInventors: Jack K. Siddens, Sivaraman Raghu
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Patent number: 4404148Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.Type: GrantFiled: September 20, 1982Date of Patent: September 13, 1983Assignee: American Cyanamid CompanyInventor: Jack K. Siddens
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Patent number: 4395415Abstract: 4-Nitro-2-trichloromethylbenzenesulfenic acid derivatives of the formula ##STR1## where R.sup.1 is nitroimidazolyl, which is substituted by alkyl, phenyl or benzyl, or R.sup.1 is S-alkyl, which is substituted by an S--S-phenyl radical, itself substituted in the phenyl moiety by nitro and trichloromethyl, or which is substituted by --O--CO--R.sup.2, where R.sup.2 is unsubstituted or substituted alkyl, unsubstituted or phenyl-substituted alkenyl, or unsubstituted or chlorine- or nitro-substituted phenyl, or monoalkylamino or dialkylamino, or unsubstituted or mono-chlorine-substituted or polychlorine-substituted aminophenyl, or R.sup.1 is --S--R.sup.3, where R.sup.3 is unsubstituted or carboxyl-substituted aryl, triazolyl, unsubstituted or alkyl-substituted thiadiazolyl, unsubstituted or alkyl-, cyano- or oxo-substituted pyridyl, or unsubstituted or alkyl-, amino-, hydroxy- or oxo-substituted pyrimidinyl, and fungicides containing these compounds.Type: GrantFiled: April 21, 1981Date of Patent: July 26, 1983Assignee: BASF AktiengesellschaftInventors: Helmut Hagen, Hans Ziegler, Celia J. Mappes, Ernst-Heinrich Pommer
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Patent number: 4388323Abstract: There are described hydroquinone-diethers endowed with a high acaricide activity, the processes for their preparation and their use as acaricides.Type: GrantFiled: March 17, 1981Date of Patent: June 14, 1983Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Angelo Longoni, Paolo Piccardi
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Patent number: 4374263Abstract: The invention relates to an esterification process employing as a heterogeneous catalyst an inorganic oxide, e.g. silica, to which there is bonded by reaction with surface hydroxyl groups a sulphonic acid-functionalized silane.Type: GrantFiled: October 24, 1980Date of Patent: February 15, 1983Assignee: The British Petroleum Company LimitedInventors: Ronald D. Hancock, Robert Mackison
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4350825Abstract: A method to synthesize styrene from toluene by: (a) oxidizing toluene to form oxygenated toluene derivatives; (b) carbonylating said oxygenated products in the presence of a carbonylation catalyst and preferably a halogen promoter to produce phenylacetic acid; (c) hydrogenating said phenylacetic acid to synthesize phenylethyl alcohol; and (d) dehydrating said phenylethyl alcohol to obtain a high yield of styrene.Type: GrantFiled: May 30, 1980Date of Patent: September 21, 1982Assignee: Exxon Research & Engineering Co.Inventor: I-Der Huang
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Patent number: 4337360Abstract: Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.Type: GrantFiled: September 28, 1979Date of Patent: June 29, 1982Assignee: Merck & Co., Inc.Inventor: Meyer Sletzinger
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Patent number: 4332959Abstract: The process is for the manufacture of phenoxylactic acids and their derivatives of the general formula: ##STR1## (in which R.sub.1 and R.sub.2, identical or different, can represent hydrogen atoms, methyl residues, methoxy groups or halogens; Y represents an OH or O--CO--R.sub.3 group with R.sub.3 representing either an aliphatic residue possibly substituted by a halogen, or an aromatic residue possibly substituted on the nucleus by one or several methyl, methoxy, halogen groups or lastly a heterocyclic group; Z represents OH group or an ##STR2## with R.sub.4 representing an alkyl or aryl radical and R.sub.5 hydrogen or an alkyl radical, NR.sub.4 R.sub.5 possibly also representing the morpholinyl radical). A cyanhydrin is subjected to a Ritter reaction (reaction with tert. butanol or isobutene in the presence of an acid).Type: GrantFiled: August 17, 1979Date of Patent: June 1, 1982Assignee: Sucreries du Soissonnais et Compagnie SucriereInventors: Jesus Anatol, Yves Clenet, Georges Bourdiau
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Patent number: 4332738Abstract: The esterification of neo acids catalyzed by the presence of a macro-reticular structured sulfonic acid cation exchange resin proceeds under mild conditions with a wide variety of alcohols to give readily recoverable esters in high yields and high purity and an easily recoverable and reusable catalyst.Type: GrantFiled: November 24, 1980Date of Patent: June 1, 1982Assignee: Exxon Research & Engineering Co.Inventors: Francisco M. Benitez, Michael F. English
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Patent number: 4331814Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.Type: GrantFiled: February 1, 1973Date of Patent: May 25, 1982Assignee: Rhone Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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Patent number: 4326055Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.Type: GrantFiled: December 15, 1978Date of Patent: April 20, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Peter Loeliger
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Patent number: 4313890Abstract: Synthetic polyol ester fluids useful as lubricants or hydraulic fluids have been prepared by the esterification of ethylene-methyl formate telomerization products with polyols containing from two to about six hydroxyl groups.Type: GrantFiled: January 29, 1980Date of Patent: February 2, 1982Assignee: Union Carbide CorporationInventors: Nan S. Chu, Nye A. Clinton, Robert A. Cupper, Philip F. Wolf, Priscilla B. Stanley