Phenolic Hydroxy Or Metallate Patents (Class 560/67)
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Patent number: 6316500Abstract: The hydroxybenzoate compounds of this invention are defined by the formula: wherein Y is hydrogen, hydroxy, halo, a C1 to C6 alkyl or a C2 to C6 alkyl ether; R is a C4 to C6 mono- or di-olefinically unsaturated hydrocarbon radical, a C4 to C7 mono- or di-acetylenically unsaturated hydrocarbon radical or a C2 to C3 acetylenically unsaturated hydrocarbon radical when at least one of X and Y is other than hydrogen and X is hydrogen, hydroxy, halo, a C1 to C6 alkyl, a C2 to C6 alkyl ether or in which A is selected from the group of X, B is selected from the group of Y and R1 is hydrogen, hydroxy, C1 to C6 alkyl, C1 to C6 alkoxy or —COOR2 in which R2 is C1 to C6 alkyl, a C2 to C6 olefinically unsaturated hydrocarbon radical or a C2 to C7 acetylenically unsaturated hydrocarbon radical.Type: GrantFiled: January 5, 1999Date of Patent: November 13, 2001Assignee: ISP Investments Inc.Inventors: Todd Elder, John J. Merianos
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Patent number: 6303052Abstract: An antioxidant composition comprising at least one compound having the formula: wherein R1 and R2 are each hydrocarbon groups having from 1 to 8 carbon atoms, a is from 1 to 3, R3 is a linear alkyl group having from 4 to 22 carbon atoms, and R4 is a linear alkyl group having from 6 to 24 carbon atoms.Type: GrantFiled: March 2, 1999Date of Patent: October 16, 2001Assignee: Condea Vista CompanyInventors: Shirley A. Moy, Kurt W. McWilliams
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Patent number: 6291703Abstract: Substituted hydroxyhydrocinnamate esters of the formula (I) where R is alkyl, n is 0 to 2, m is 1 to 4 and A is alkyl, interrupted or uninterrupted alkylene, alkanetriyl or pentaerythrityl, are prepared by continuous transesterification of the corresponding lower alkyl mono-ester with an alkanol or polyol of the formula A-(OH)m. This novel process comprises continuously introducing into and reacting the reactants in a heated distillation column reactor having a reaction zone which contains a solid, heterogeneous transesterification catalyst to form the compound of formula (I) and the corresponding lower alkanol; separating the products so formed based on their difference in volatility; and continuously removing said products from the distillation column at a steady rate, thereby preventing the reaction mixture from reaching chemical equilibrium.Type: GrantFiled: January 28, 1999Date of Patent: September 18, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Robert Anthony Schaerfl, Jr., Michael James Day, Sean Peter Piecuch, Ronald Robert Tellier
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Patent number: 6288260Abstract: A two step process is described for making 2-alkyl-3-hydroxybenzoic acids or derivatives of benzoic acids by first reacting an allenyl ester or equivalent with furan followed by the ring-opening reaction of the derived bicyclo intermediate with base. The benzoic acids thus prepared are useful intermediates for the preparation of agricultural and pharmaceutical materials.Type: GrantFiled: December 7, 1999Date of Patent: September 11, 2001Assignee: Rohm and Haas CompanyInventor: Martha Jean Kelly
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Patent number: 6258974Abstract: There are disclosed amphoteric nano-sized metal oxide particles functionalized with silyl esters of a phosphonate and composites thereof with an acrylate-based monomer, including liquid crystal monomers photopolymerizable at ambient temperature. Also disclosed are the method making such functionalized particular by reacting a metal oxide with a silyl ester of a phosphonate in the presence of a non-aqueous solvent and in an inert atmosphere and the method of making the composites wherein the functionalized particles are admixed with an acrylate-based matrix monomer, including liquid crystal monomers photopolymerizable at ambient temperature. Further disclosed is the method of dental repair wherein the composites are applied to a tooth and photopolymerized.Type: GrantFiled: June 23, 1998Date of Patent: July 10, 2001Assignee: Southwest Research InstituteInventors: Stephen T. Wellinghoff, Hong Dixon, Henry R. Rawls, Barry K. Norling
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Patent number: 6207857Abstract: The compounds of the formula I are precursors for organoleptic and antimicrobial compounds. The latter are generated in the presence of skin bacteria, enzymes or acidic or alkaline conditions. One precursor molecule can provide one or more different compounds.Type: GrantFiled: June 23, 1998Date of Patent: March 27, 2001Assignee: Givaudan-Roure (International) S.A.Inventors: Denise Anderson, Georg Frater
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Patent number: 6187950Abstract: Compounds of the formula Y3(R4)—X—Y1(R1R2)—Z—Y2(R2)—A—B where the symbols have the meaning defined in the specification, have retinoid, retinoid antagonist or retinoid inverse agonist type biological activity.Type: GrantFiled: March 12, 1999Date of Patent: February 13, 2001Inventors: Tae K. Song, Min Teng, Roshantha A. Chandraratna
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Patent number: 6184411Abstract: The invention is directed to an improved process for the preparation of a compound of formula (I) wherein R is alkyl, n is 0 to 2, m is 1 to 4 and A is alkyl, interrupted or uninterrupted alkylene, alkanetriyl or pentaerythrityl, by transesterifying the corresponding lower alkyl with a higher alkanol of the formula A-(OH)m in the presence of a tin catalyst; wherein the improvement comprises reacting the tin catalyzed transesterification reaction mass with a carboxylic acid or hydrate thereof neat, in the absence of an aqueous medium, until the tin catalyst forms an insoluble derivative, and then separating the insoluble derivative from the reaction mass by filtration without the assistance of a filtration aid. The invention allows for a convenient method by which to remove the residual tin catalyst from the substituted hydroxyphenylcarboxylic acid ester compounds of formula (I).Type: GrantFiled: January 28, 1999Date of Patent: February 6, 2001Assignee: Ciba Specialty Chemicals CorporationInventor: John Richard Ross
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Patent number: 6043360Abstract: The instant invention provides intermediates and processes for the preparation of compounds of formula IV ##STR1## wherein: n is 0, 1, or 2;R is hydrogen or C.sub.1 -C.sub.4 alkyl;X.sup.1 is hydrogen, cyano, 4-hydroxybenzoyl, 4-halobenzoyl, or 4-(C.sub.1 -C.sub.4 alkoxy)benzoyl;Y is NR.sup.4 R.sup.5, 4-hydroxyphenyl, or 4-(C.sub.1 -C.sub.4 alkoxy)phenyl;and R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: April 29, 1998Date of Patent: March 28, 2000Assignee: Eli Lilly and CompanyInventors: Tony Yantao Zhang, John Paul Gardner
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Patent number: 5973072Abstract: The present invention is directed to a polymeric vehicle, the formulated coating composition and a coating binder made from the polymeric vehicle and a method for making the polymeric vehicle where the polymeric vehicle includes a phenolic urethane reactive diluent. The phenolic urethane reactive diluent may be made from a phenolic ester alcohol having at least one aliphatic hydroxyl group.Type: GrantFiled: March 21, 1996Date of Patent: October 26, 1999Assignee: Exxon Chemical Patents, Inc.Inventors: Frank N. Jones, Vijay Swarup, Ramachandran P. Subrayan, Suru Zhang
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Patent number: 5948922Abstract: Compounds containing two cyclic hydrocarbon moieties which are substituted to provide crosslinking functionality and which are linked to each other by secondary or tertiary oxycarbonyl containing moiety are basis for compositions which are cured to provide cured thermosets for encapsulation and underfill for electronic components that are thermally decomposable to allow repair, replacement, recovery or recycling of operative electronic components from assemblies that are inoperative.Type: GrantFiled: February 20, 1997Date of Patent: September 7, 1999Assignee: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Hilmar Koerner
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Patent number: 5938973Abstract: A swallow-tailed compound of the following general formula (1), ##STR1## wherein m is an integer of 4 to 10, n is an integer of 2 to 6, p is 0 or 1 and each of X and Y is independently a hydrogen or fluorine atom; and a ferrielectric liquid crystal composition consisting essentially of the swallow-tailed compound of the general formula (1) and a ferrielectric liquid crystal compound of the following general formula (2), ##STR2## wherein R is a linear alkyl group having 6 to 12 carbon atoms, Z is a hydrogen or fluorine atom, r is an integer of 2 to 4 and s is an integer of 2 to 4. The ferrielectric liquid crystal composition has a ferrielectric phase in a broad temperature range and attains a fast response and a large tilt angle in a broad temperature range so that a ferrielectric liquid crystal display device having high display qualities can be provided.Type: GrantFiled: September 11, 1997Date of Patent: August 17, 1999Assignee: Mitsubishi Gas Chemical CompanyInventors: Yuki Motoyama, Tomoyuki Yui, Masahiro Johno, Takahiro Matsumoto
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Patent number: 5886209Abstract: A multi-stage catalytic process for preparing a 2-(4-hydroxyphenoxy)-propionate, especially methyl 2-(4-hydroxyphenoxy)-propionate, with a purity greater than 99% by esterifying the corresponding 2-(4-hydroxyphenoxy)-propionic acid with an excess amount of alcohol, e.g. methyl alcohol, in a series of at least 2 up to 10 sequential stages at temperatures of 20.degree. to 150.degree. C. and pressures of 0.05 to 5 bar in the presence of a distillable acid catalyst such as hydrochloric acid or hydrogen chloride. In a first esterification stage, unreacted alcohol is removed from the ester product in vacuo at temperatures of 30.degree. to 100.degree. C. together with other volatile components, including the acid catalyst. Without a separate purification of the resulting ester as the bottoms product of the first stage, the esterification step is repeated in at least one additional stage. The final ester product of this multi-stage process is characterized by a water content of less than 0.Type: GrantFiled: September 6, 1996Date of Patent: March 23, 1999Assignee: BASF AktiengesellschaftInventors: Thomas Wettling, Manfred Dimmler, Bernd Hupfeld, Jochem Henklemann
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Patent number: 5874608Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms or OR, NHR, NR.sub.2, SR or COOR, in which R is an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R shown in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.2, in which R has the above meaning, in the presence of a water-insoluble tertiary amine and water at a temperature of 10.degree.Type: GrantFiled: May 19, 1997Date of Patent: February 23, 1999Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5866710Abstract: A process for the preparation of an ester comprises carrying out an esterification in the presence of a catalyst comprising the reaction product of an orthoester or a condensed orthoester of titanium or zirconium, an alcohol containing at least two hydroxyl groups, a 2-hydroxy acid and a base. The process can be a direct esterification or a transesterification and can be a polyesterification. The catalyst can effectively produce esters without leading to a haze in the final product and there is a reduced amount of yellowing of polyesters in comparison to known catalysts.Type: GrantFiled: June 5, 1997Date of Patent: February 2, 1999Assignee: Tioxide Specialties LimitedInventors: John Ridland, Iain Wesley Hepplewhite, Brian Steven Jolly
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Patent number: 5744628Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OR, NHR, NR.sub.2, SR or COOR, R being an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R identified in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.Type: GrantFiled: July 29, 1996Date of Patent: April 28, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5713966Abstract: Polyalkyl hydroxyaromatic esters having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 is a polyalkyl group having a weight average molecular weight in the range of about 450 to 5,000; and x is an integer from 0 to 10.The polyalkyl hydroxyaromatic esters of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: April 16, 1996Date of Patent: February 3, 1998Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5686398Abstract: There are herein disclosed an additive for a lubricant or a fuel which comprises at least one selected from the group consisting of substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II) ##STR1## wherein R.sup.1 to R.sup.5 are each an organic group having 6 or more carbon atoms, a, b, d, e, k and m are from 1 to 3, c, f, g, i and j are from 0 to 3, and h is from 0 to 4, but (f+g) is from 1 to 3, and (h+i) is from 1 to 6, an additive composition for a lubricant or a fuel, and a lubricating oil composition or a fuel composition containing the above-mentioned additive.The above-mentioned additive for the lubricant or the fuel is desirable as an ashless detergent excellent in high-temperature stability in place of a metal detergent, and the lubricating oil composition or the fuel composition containing this additive can suitably be used as the lubricant or the fuel for an internal combustion engine which can comply with future exhaust gas controls.Type: GrantFiled: December 6, 1995Date of Patent: November 11, 1997Assignee: Idemitsu Kosan Co., Ltd.Inventors: Tomiyasu Minokami, Hiroaki Koshima, Harutomo Ikeda, Masahisa Gotoh
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Patent number: 5654331Abstract: Diaromatic compounds, characterised in that they correspond to the following general formula: ##STR1## in which: R.sub.1 is --CH.sub.3, --CH.sub.2 OH, --COR.sub.8 or --CH.sub.2 OCOR.sub.9, R.sub.8 is H, OH, --OR.sub.10, --N(rr') or alkyl, R.sub.10 is alkyl, alkenyl, aryl or aralkyl, r and r' being H, alkyl, aryl, aralkyl, etc., r and r' together form a heterocycle, R.sub.9 is alkyl, alkenyl or a sugar residue, R.sub.2 and R.sub.3 are --OR.sub.11 or --OCOR.sub.11, R.sub.11 is H, alkyl, fluoroalkyl, aryl or aralkyl, R.sub.3 in addition being H, R.sub.4 is H, OH, alkyl, alkoxy, F, Cl or --CF.sub.3, R.sub.5 and R.sub.7 are H, OH, alkoxy, .alpha.-substituted alkyl or .alpha.,.alpha.'-disubstituted alkyl, etc., R.sub.6 is H, OH, alkyl, alkoxy, cycloalkyl, etc., R.sub.5 and R.sub.7 cannot simultaneously be OH or alkoxy and R.sub.4, R.sub.5, R.sub.6 and R.sub.7 cannot simultaneously be H, R.sub.5 and R.sub.6 or R.sub.6 and R.sub.Type: GrantFiled: May 25, 1995Date of Patent: August 5, 1997Assignee: Centre International De Recherches Dermatologiques Galderma (Cird Galderma)Inventor: Jean-Michel Bernardon
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Patent number: 5563291Abstract: There is disclosed a process for the preparation of compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 -C.sub.8 alkyl or cyclopentyl or cyclohexyl,m is 0, 1, 2 or 3,n is 1 or 2, andR.sub.3, depending on the value of n, is C.sub.4 -C.sub.20 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.2 -C.sub.4 alkylene, or C.sub.4 -C.sub.12 alkylene which is interrupted by oxygen,by reaction of a compound of formula II ##STR2## wherein R is methyl or ethyl, with a compound of formula IIIR.sub.3 (OH).sub.n (III)which reaction is carried out in the presence of magnesium acetate as catalyst.Type: GrantFiled: March 7, 1995Date of Patent: October 8, 1996Assignee: Ciba-Geigy CorporationInventor: Christoph Kleiner
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Patent number: 5498795Abstract: Compounds of the formula ##STR1## wherein R.sub.1 -R.sub.3 and R.sub.5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R.sub.4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R.sub.5 group defined above; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.Type: GrantFiled: December 29, 1994Date of Patent: March 12, 1996Assignee: Allergan, Inc.Inventors: Tae K. Song, Roshantha A. Chandraratna
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Patent number: 5498748Abstract: An anthracene derivative having at least two groups of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl, alkoxy, etc., is particular effective for forming an antireflection coating for preventing multiple reflection of exposing light from a highly reflective substrate, etc.Type: GrantFiled: July 11, 1994Date of Patent: March 12, 1996Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Fumiyoshi Urano, Keiji Oono, Hiroshi Matsuda
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Patent number: 5488135Abstract: The invention concerns the compounds of formula I ##STR1## wherein the substituents have various significances, in free form and, where such forms exist, in salt form. The compounds have potent antihyperproliferative/antiinflammatory and anticancer activity.Type: GrantFiled: October 16, 1992Date of Patent: January 30, 1996Assignee: Sandoz Ltd.Inventors: Peter Nussbaumer, Anton Stutz
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Patent number: 5476860Abstract: Diaromatic compounds, characterized in that they correspond to the following general formula: ##STR1## in which: R.sub.1 is --CH.sub.3, --CH.sub.2 OH, --COR.sub.8 or --CH.sub.2 OCOR.sub.9, R.sub.8 is H, OH, --OR.sub.10, --N(rr') or alkyl, R.sub.10 is alkyl, alkenyl, aryl or aralkyl, r and r' being H, alkyl, aryl, aralkyl, etc., r and r' together form a heterocycle, R.sub.9 is alkyl, alkenyl or a sugar residue, R.sub.2 and R.sub.3 are --OR.sub.11 or --OCOR.sub.11, R.sub.11 is H, alkyl, fluoroalkyl, aryl or aralkyl, R.sub.3 in addition being H, R.sub.4 is H, OH, alkyl, alkoxy, F, Cl or --CF.sub.3, R.sub.5 and R.sub.7 are H, OH, alkoxy, .alpha.-substituted alkyl or .alpha.,.alpha.'-disubstituted alkyl, etc., R.sub.6 is H, OH, alkyl, alkoxy, cycloalkyl, etc., R.sub.5 and R.sub.7 cannot simultaneously be OH or alkoxy and R.sub.4, R.sub.5, R.sub.6 and R.sub.7 cannot simultaneously be H, R.sub.5 and R.sub.6 or R.sub.6 and R.sub.Type: GrantFiled: December 8, 1993Date of Patent: December 19, 1995Assignee: Centre International de Recherches Dermatologiques (CIRD Galderma)Inventor: Jean-Michel Bernardon
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Patent number: 5426212Abstract: The reaction of methyl p-hydroxybenzoate and a .alpha.,.omega.-alkanediol, in the presence of a transesterification catalyst, such as a metal alkoxide and/or metal acetate, can be used to synthesize an .alpha.,.omega.-bis(p-hydroxybenzoyloxy)alkane monomer.Type: GrantFiled: August 26, 1993Date of Patent: June 20, 1995Assignee: Akzo Nobel N.V.Inventors: Ki-Soo Kim, Sophia Dashevsky, Stanley W. Palmaka
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Patent number: 5416235Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.Type: GrantFiled: November 1, 1993Date of Patent: May 16, 1995Assignee: Octel Chemicals LimitedInventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
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Patent number: 5399673Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.Type: GrantFiled: February 9, 1993Date of Patent: March 21, 1995Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 5334749Abstract: A polymerizable phenol compound represented by the formula (I): ##STR1## wherein X represents a hydrogen atom, an alkyl group, a halogen atom, an alkylsulfonyl group, a hydroxyl group or a substituted or unsubstituted phenyl group; Y represents a hydrogen atom, a hydroxyl group, an alkoxy-carbonyl group, a halogen atom, an alkyl group, an alkyl-sulfonyl group, an alkoxy group, an alkanoyloxy group, an acryloyloxy group or a methacryloyloxy group; Z represents --COO--, --O--, --SO.sub.2 -- or --SO.sub.2 NH--; R represents a divalent linkage group having an --O--, --S--, --SO.sub.2 --, --CO--, --NH--, or a cyclic structure; and P represents an acryloyloxy group or a methacryloyloxy group.Type: GrantFiled: December 17, 1992Date of Patent: August 2, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Yuuichi Fukushige, Ken Iwakura, Masato Satomura
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Patent number: 5332858Abstract: The invention relates to a method for preparing an ester composition in which at least one activated phenolic ether group of a molecule is reacted with at least one haloformyl group of another molecule.Type: GrantFiled: July 17, 1992Date of Patent: July 26, 1994Assignee: Shell Oil CompanyInventors: Feike De Jong, Jan H. H. Meurs
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Patent number: 5324857Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from certain problems, especially in the presence of transition metals. These problems include both in situ generation of impurities and particularly nitrosamines, which are allegedly carcinogenic, and also impaired product formation. The problems can be ameliorated by employing in the reaction mixture free radical scavengers, including in particular phenols and polyhydroxy-substituted aromatic compounds. The scavengers are advantageously employed in conjunction with a metal chelating agent such as polycarboxylic acid or an organopolyphosphonic acid.Type: GrantFiled: April 28, 1992Date of Patent: June 28, 1994Assignee: Solvay InteroxInventor: Noel S. Shehad
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Patent number: 5310773Abstract: Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.Type: GrantFiled: June 4, 1992Date of Patent: May 10, 1994Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Eduard K. Kleiner
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Patent number: 5296601Abstract: A process for producing a carboxylic acid ester, which comprises reacting an organic chloride having at least one chlorine atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide and an amine or an alcohol in the presence of a base by using as catalysts a palladium compound and a phosphine compound represented by the general formula (V):(R).sub.2 P--X--P(R).sub.2 (V)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.Type: GrantFiled: May 27, 1992Date of Patent: March 22, 1994Assignee: Nihon Nohyaku Co., Ltd.Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
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Patent number: 5274170Abstract: Compounds of the formula ##STR1## in which R is hydrogen or hydroxyl, R.sub.1 is alkyl, alkoxy, amino or aryl, and R.sub.2 is hydrocarbylcarbonyl or hydrocarbylsulfonyl, are highly suitable for stabilizing magenta couplers in photographic materials.Type: GrantFiled: June 15, 1992Date of Patent: December 28, 1993Assignee: Ciba-Geigy CorporationInventors: David G. Leppard, David H. Steinberg, Henri Dubas
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Patent number: 5227514Abstract: Salicylic acid esters of carnitine are distinguished relative to acetylsalicylic acid by high water solubility, low toxicity and good stomach tolerance. The compounds are obtainable in three stages from carnitine hydrochloride and o-methoxybenzoyl chloride.Type: GrantFiled: February 11, 1992Date of Patent: July 13, 1993Assignee: Lonza Ltd.Inventors: Thomas Meul, Jacques Deshusses
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Patent number: 5225588Abstract: Hydroxybenzoates such as methylsalicylate are alkylated by reacting a hydroxybenzoate with a polyalphaolefin in the presence of a catalytic amount of SnCl.sub.4.Type: GrantFiled: February 3, 1992Date of Patent: July 6, 1993Assignee: Ethyl CorporationInventors: K. Pushpananda A. Senaratne, Patrick S. Bynum
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Patent number: 5223637Abstract: KS-506a, KS-506x and KS-506g having an activity to inhibit cyclic nucleotide phosphodiesterase and KS-506m and KS-506h having an activity to inhibit histamine release are produced by culturing a microorganism belonging to the genus Mortierella.Type: GrantFiled: May 28, 1992Date of Patent: June 29, 1993Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Kazutoshi Kuroda, Hiroshi Kase, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Joji Goto, Koji Yamada
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Patent number: 5202458Abstract: Compounds of the formula I or II ##STR1## in which R, R.sup.0, R.sup.1 and R.sup.2 are as defined in claim 1. The compounds, some of which are novel, are light stabilizers for color photographic recording materials.Type: GrantFiled: August 5, 1991Date of Patent: April 13, 1993Assignee: Ciba-Geigy AGInventor: David G. Leppard
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Patent number: 5198571Abstract: A region-specific monofunctionalization of a phenolic hydroxy onto a polyphenol for the preparation of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --CN, formyl, carboxy, alkoxy carbonyl of up to 9 carbon atoms, aralkoxy carbonyl or up to 12 carbon atoms and halogen and R' is a hydroxy protective group comprising reacting a polyphenol of the formula ##STR2## wherein R has the above definition with a base to form the corresponding dianion, reacting the latter with a trialkyl borate of the formulaB(OAlk).sub.3wherein Alk is alkyl of 1 to 6 carbon atoms to form a compound of the formula ##STR3## reacting the latter with a reagent capable of introducing a hydroxy protective group and reacting the latter with a hydrolysis agent for the oxygen-boron bond to obtain the corresponding compound of Formula I.Type: GrantFiled: December 16, 1991Date of Patent: March 30, 1993Assignee: Roussel UclafInventors: Jean-Louis Brayer, Daniel Calvo, Francois Ottello
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Patent number: 5196565Abstract: The present invention relates to a process for the manufacture of granules of low-melting alkyl ester containing hindered hydroxylphenyl groups, which comprises(a) extracting a melt of crude alkyl ester containing hindered hydroxylphenyl groups with an aqueous alcoholic solution of N,N-dibenzylhydroxylamine (DBHA),(b) granulating the extracted melt by introducing said melt into an aqueous alcoholic solution maintained under a turbulent state at a temperature below 20.degree. C., and(c) isolating the resulting granules.Type: GrantFiled: June 26, 1992Date of Patent: March 23, 1993Assignee: Ciba-Geigy CorporationInventor: John R. Ross
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Patent number: 5177246Abstract: The novel compounds of the formulae Ia and Ib ##STR1## in which the radicals R are identical or different and are a group of the formula II ##STR2## in which X is a direct bond, methylene, ethylene or a group ##STR3## and Y is C.sub.1 -C.sub.8 alkyl, R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.7 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl, or are phenyl or C.sub.7 -C.sub.10 phenylalkyl, and R.sub.2 is additionally hydrogen, are suitable for stabilizing organic material against thermal, oxidative or actinic degradation.Type: GrantFiled: August 23, 1991Date of Patent: January 5, 1993Assignee: Ciba-Geigy CorporationInventor: Rita Pitteloud
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Patent number: 5162405Abstract: The present invention comprises novel single-functional and mixtures of multi-functional oligomeric performance additive compounds having one or more components of Structure A R1 ? ? ##STR1## (The definitions of R, Z1, Z2, Z3, A1, A2, A3 and y are given in the Summary Section), their uses and polymeric compounds and compositions containing them which have enhanced oxidative stabilities, enhanced ultraviolet (UV) and light stabilites and/or enhanced flame retardance. An example is the bis sulfonic acid bispotassium salt reaction product from an oligomeric caprolactone diol (TONE.RTM. 260), 2-sulfobenzoic acid anhydride and potassium carbonate, and use of this product, at levels up to about 3.0%, in a general purpose bisphenol A polycarbonate resin, to enhance the fire resistance or flame retardance of the polycarbonate resin.Type: GrantFiled: March 22, 1991Date of Patent: November 10, 1992Assignee: ELF Atochem North America, Inc.Inventors: Ronald E. MacLeay, Jose Sanchez, Daryl L. Stein
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Patent number: 5155244Abstract: A method of solubilizing a first compound in a second medium where the first compound has a limited solubility in the second medium. In particular, the method comprises reacting the first compound with the second medium. By this reaction, a product is formed whereby an active component of the first compound is covalently incorporated into the second medium.The first compound and second medium each contain at least one reactive group which will react with a reactive group of the other. In addition, the first compound comprises at least one antioxidant which will be covalently bonded to and thus effectively solubilized in the second medium by the reaction.The second medium comprises glyceride derivatives, silicones, fluorocarbons and alkoxylates containing reactive groups such as hydroxy, amino, carboxyl, ester, or amides.Type: GrantFiled: February 28, 1990Date of Patent: October 13, 1992Assignee: Karlshamns ABInventors: George H. Greene, James C. Phillips, Jerry F. Stults, Jan P. E. Tellings
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Patent number: 5144058Abstract: Tetrakis [3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane in the form of grained alpha-form crystals having improved coloration. The above compound is prepared by transesterifying low-alkyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate with pentaerythritol in the presence of catalyst and aliphatic hydrocarbons as reaction solvent.Type: GrantFiled: June 15, 1990Date of Patent: September 1, 1992Assignee: International Chemical Consultant, Ltd.Inventor: Atsushi Nishimura
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Patent number: 5130454Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.Type: GrantFiled: December 19, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
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Patent number: 5114613Abstract: An optically active lactic acid derivative represented by the following formula (I): ##STR1## wherein R represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1 to 18 carbon atoms; C* represents an asymmetric carbon atom; l is 0 or 1; m is 1 or 2; A represents a group selected from the following groups (a) and (b):(a) hydroxyl group, halogen, benzyloxy group, phenoxy group, toluenesulfonic acid group, acetyloxy group, trifluoroacetyloxy group; ##STR2## (wherein R' is an alkyl group or alkoxy group having 4 to 18 carbon atoms, n is 0 or 1, ##STR3## with proviso that when A is selected from the groups in the above group (a), l is 1 and m is 1 or 2; and when A is selected from the groups in the above group (b), m=n=1 when l is 0, or m and n are 0, 1 or 2 and m+n is 1 or 2 when l is 1, and ##STR4##Type: GrantFiled: September 13, 1989Date of Patent: May 19, 1992Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Akira Tsuboyama, Hiroyuki Kitayama, Kenji Shinjo, Chieko Hioki
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Patent number: 5098477Abstract: Inks, particularly inks for ink jet printing, contain at least one compound of the formula I ##STR1## as a stabilizer. The symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.3 ' and R.sub.4 ' are as defined in claim 1. The compounds are in part novel and are suitable for use as light stabilizers for organic materials.Type: GrantFiled: December 8, 1989Date of Patent: March 24, 1992Assignee: Ciba-Geigy CorporationInventors: Eric Vieira, Hugh S. Laver
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Patent number: 5086067Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH-- or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.Type: GrantFiled: December 18, 1989Date of Patent: February 4, 1992Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
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Patent number: 5072023Abstract: A process is described in which a lactone ##STR1## is reacted with an alkylester X.sup.1 --CH.sub.Type: GrantFiled: February 15, 1990Date of Patent: December 10, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Jeffrey A. Robl
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Patent number: 5051527Abstract: The invention lies in novel ferroelectric liquid crystal compounds particularly represented by the general formulae, having a good responsibility in relation to the applied electric field and a wide range of phase transition points inclusive of the room temperature so as to be useful alone as the liquid crystal material but also to be mixed with other liquid crystal compounds for expanding the phase transition points to a desired range and making the response speed of the liquid crystal composition faster. ##STR1## In the formulae, m and n are same or different with each other and represent an integral of 1-20.Type: GrantFiled: February 28, 1989Date of Patent: September 24, 1991Assignee: Showa Shell Sekiyu K.K.Inventors: Yoshiichi Suzuki, Takashi Hagiwara, Hiroyuki Mogamiya
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Patent number: 4973737Abstract: Highly pure benzyl esters of aromatic hydroxycarboxylic acids are produced in high yields by reacting an aromatic hydroxycarboxylic acid or its lower alkyl ester with a benzyl alcohol in the presence of an organotin compound of the general formula ##STR1## wherein R's are identical or different and each represents an alkyl group having 1 to 8 carbon atoms or an aryl group, and Z represents an oxygen or sulfur atom,an organotin compound of the general formulaR.sub.p SnX.sub.q (II)wherein R is as defined, X represents a halogen atom or the group --OCOR.sup.1 in which R.sup.1 represents a saturated or unsaturated alkyl group having 1 to 18 carbon atoms or an aryl group, p is 2, 3 or 4, q is 0, 1 or 2, the sum of p and q is 4, and when q is 2, the two X's may be linked to each other to form the group --OCO--R.sup.2 --COO-- in which R.sup.2 represents a saturated or unsaturated alkylene group having 1 to 10 carbon atoms or an arylene group,or an organotitanium compound of the general formulaTi(OR).sub.Type: GrantFiled: January 30, 1989Date of Patent: November 27, 1990Assignee: Kabushiki Kaisha Veno Seiyaku Oyo KenkyuoInventors: Ryuzo Ueno, Hiroaki Tsuchiya, Shigeru Itoh, Ichiro Yamamoto