Esterified Phenolic Hydroxy Patents (Class 560/130)
  • Patent number: 6111133
    Abstract: Substituted styrenes are synthesized by a simple, low temperature technique. A protected phenol styrene is reacted with an acid anhydride, dicarbonate, a halogen substituted alkyl, or an acid chloride in the presence of base to form a carbonyl substituted styrene. Unexpected yield decrease due to distillation is avoided because the product is sufficiently pure to be used without such distillation.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: August 29, 2000
    Assignee: Lucent Technologies Inc.
    Inventor: Francis Michael Houlihan
  • Patent number: 6077877
    Abstract: The present invention provides amine/amide catalysts for use in catalyzing the formation of polyurethane. The amine/amide catalysts, which have low fugitivity due to their reactivity with isocyanates, and good catalytic activity, have the structure ##STR1## wherein Q is C.sub.z H.sub.2z+1, or (CH.sub.2).sub.n N(R.sup.3).sub.k T, T is a monovalent C.sub.1 -C.sub.4 alkyl, amino-C.sub.1 -C.sub.4 -alkyl, mono-C.sub.1 -C.sub.4 -alkylamino-C.sub.1 -C.sub.4 -alkyl, or di-C.sub.1 -C.sub.4 -alkylamino-C.sub.1 -C.sub.4 -alkyl group, or T is a divalent alkyl, amine substituted alkyl, alkylaminoalkyl, or alkoxyalkyl group which forms with the nitrogen atom shown in structure (I) to which T is attached a cyclic structure which incorporates up to 6 carbon atoms in the ring as well as the nitrogen atom shown in structure (I), which cyclic structure may be substituted with C.sub.1 to C.sub.4 alkyl;k=0 or 1, being 1 if T is a monovalent group and 0 if T is a divalent group; R.sup.2 .dbd.H or C.sub.z H.sub.2z+1 ; R.sup.3 .dbd.
    Type: Grant
    Filed: April 3, 1997
    Date of Patent: June 20, 2000
    Assignee: CK Witco Corporation
    Inventors: Richard M. Gerkin, K. Kaye Robinson
  • Patent number: 6077970
    Abstract: The present invention relates to carboxylic acid esters of 2-hydroxy-5-isoalkyl-beta-methylstyrenes wherein the said isoalkyl substituent comprises 8-18 carbon atoms.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: June 20, 2000
    Assignee: Henkel Corporation
    Inventor: Leroy Krbechek
  • Patent number: 6066757
    Abstract: A stilbene compound is disclosed which has the following general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 each stand for hydrogen, an alkyl group or an acyl group and Ar.sup.1 and Ar.sup.2 each stand for a monovalent homocyclic aromatic group. The stilbene compound may be incorporated into a photoconducting layer of an electrophotographic photoconductor as a charge transporting material. A process for the production of the stilbene compound is also disclosed.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: May 23, 2000
    Assignee: Ricoh Company, Ltd.
    Inventors: Chiaki Tanaka, Masaomi Sasaki, Tomoyuki Shimada
  • Patent number: 6051732
    Abstract: The present invention relates to a process for the preparation of 3-acetoxy-2-methylbenzoyl chloride by reacting an alkali metal salt of 3-aminonaph-thalene-1,5-disulfonic acid with alkali metal hydroxide and water in the weight ratio 1:(1 to 1.6):(1 to 1.6) at 220 to 320.degree. C. to give the dialkali metal salt of the 3-hydroxy-2-methylbenzoic acid, separating off insoluble constituents from the reaction mixture, then adjusting the reaction mixture to a pH of 11.5 to 13.5 by addition of acid and reacting with acetic anhydride at -5 to +25.degree. C., precipitating the 3-acetoxy-2-methylbenzoic acid by addition of acid, separating off the 3-acetoxy-2-methylbenzoic acid and reacting it with an inorganic acid chloride to give 3-acetoxy-2-methylbenzoyl chloride.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: April 18, 2000
    Assignee: Clariant GmbH
    Inventors: Robert Cosmo, Andreas Dierdorf
  • Patent number: 6040339
    Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is alkyl; R.sup.2a, R.sup.2b, R.sup.2c and R.sup.2d are the same or different and each is hydrogen, optionally substituted alkyl or various other organic groups; R.sup.3 is alkyl; R.sup.4 is a group of formula (II), (III), (IV), (V), (VI), (VII), (VIII) or (IX): ##STR2## wherein: A.sup.1 is a single bond, alkylene or alkenylene; A.sup.2 is or alkenylene; A.sup.3 is a single bond, alkyleneor alkenylene; R.sup.5a and R.sup.5b are the same or different and each is hydrogen, alkyl or various other groups; R.sup.6 is alkyl or phenyl; R.sup.7 is hydrogen or alkyl; R.sup.8 is alkyl or various other groups; and n is 0 and pharmaceutically acceptable salts thereof have valuable inhibitory activity against acyl-CoA: cholesterol acyl transferase.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: March 21, 2000
    Assignee: Sankyo Company, Limited
    Inventors: Akira Yoshida, Kozo Oda, Takashi Kasai, Kousei Shimada, Hiroshi Kogen, Ichiro Hayakawa, Sadao Ishihara, Teiichiro Koga, Eiichi Kitazawa, Taro Tokui
  • Patent number: 5993780
    Abstract: The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula I ##STR1## (wherein n is 0 or 1, and where n is 1 each C.sub.6 R.sub.5 moeity may be the same or different; each group R is a hydrogen atom, an iodine atom or a hydrophilic moiety M or M.sub.1, two or three non-adjacent R groups in each C.sub.6 R.sub.5 moiety being iodine and at least one, and preferably two or three, R groups in each C.sub.6 R.sub.5 moiety being M or M.sub.1 moieties; X denotes a bond or a group providing a 1 to 7 atom chain linking two C.sub.6 R.sub.5 moieties or, where n is 0, X denotes a group R; each M independently is a non-ionic hydrophilic moiety; and each M.sub.1 independently represents a C.sub.1-4 alkyl group substituted by at least one hydroxyl group and optionally linked to the phenyl ring via a carbonyl, sulphone or sulphoxide group, at least one R group being an M.sub.1 moiety; with the proviso that where n is zero either at least one M.sub.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: November 30, 1999
    Assignee: Nycomed Imaging AS
    Inventors: Torsten Almen, Sven Goran Andersson, Lars-Goran Wistrand, Klaes Golman, .O slashed.yvind Antonsen, Rune Fossheim, Unni Nordby Wiggen, H.ang.kan Wikstrom, Tomas Klingstedt, Ib Leunbach, Arne Berg, Harald Dugstad
  • Patent number: 5985927
    Abstract: Medicinal products for the selective control of tumor tissue and a method for control of such tumor tissue by administration of such product to a host. The products comprise: (a) two different compounds having a pH below 7 when the compounds are present in a protonated form, such compounds having the formula set forth below and (b) a pharmaceutically acceptable inert medicinal product carrier. The compounds have the following ##STR1## wherein R.sub.1 is hydrogen or a moiety which completes an ester group or an ether group, R.sub.2 is independently selected from the group consisting of an amino group, hydroxyl, an ester group, an ether group and a halogen, and n is an integer of 1 to 4.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 16, 1999
    Inventor: Werner Kreutz
  • Patent number: 5973072
    Abstract: 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: Grant
    Filed: March 21, 1996
    Date of Patent: October 26, 1999
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Frank N. Jones, Vijay Swarup, Ramachandran P. Subrayan, Suru Zhang
  • Patent number: 5965766
    Abstract: Nucleophilic substitution reactions on halobenzenes or triflyl substituted benzenes are carried out in the presence of catalysts. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids and optionally substituted hydroxybenzonitriles and alkoxybenzonitriles from substituted 2,6-dihalobenzenes, 2-halo-6-triflylbenzene and 2,6-ditriflylbenzenes.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: October 12, 1999
    Assignee: Rohm and Haas Company
    Inventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
  • Patent number: 5962725
    Abstract: HIV protease inhibitors inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds can be prepared by the novel methods of the present invention using the novel inventive compounds and intermediates.
    Type: Grant
    Filed: September 5, 1997
    Date of Patent: October 5, 1999
    Assignees: Agouron Pharmaceuticals, Inc., Japan Tobacco, Inc.
    Inventors: Michael E. Deason, Kathleen R. Whitten
  • Patent number: 5925674
    Abstract: This invention relates to cycloalkylcarboxanilides of the formula ##STR1## which are used to combat pests.
    Type: Grant
    Filed: October 26, 1995
    Date of Patent: July 20, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Krueger, Klaus Sasse, Thomas Schenke, Michael Negele, Heinz-Wilhelm Dehne
  • Patent number: 5886238
    Abstract: Alkene precursors for preparing dialkyl-substituted dioxetanes. The dioxetanes are useful for the detection of triggering agents including enzymes.
    Type: Grant
    Filed: August 28, 1996
    Date of Patent: March 23, 1999
    Assignees: Lumigen, Inc., The Board of Governors of Wayne State University
    Inventors: Arthur Paul Schaap, Hashem Akhavan-Tafti
  • Patent number: 5882628
    Abstract: The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula I ##STR1## (wherein n is 0 or 1, and where n is 1 each C.sub.6 R.sub.5 moeity may be the same or different; each group R is a hydrogen atom, an iodine atom or a hydrophilic moiety M or M.sub.1, two or three non-adjacent R groups in each C.sub.6 R.sub.5 moiety being iodine and at least one, and preferably two or three, R groups in each C.sub.6 R.sub.5 moiety being M or M.sub.1 moieties; X denotes a bond or a group providing a 1 to 7 atom chain linking two C.sub.6 R.sub.5 moieties or, where n is 0, X denotes a group R; each M independently is a non-ionic hydrophilic moiety; and each M.sub.1 independently represents a C.sub.1-4 alkyl group substituted by at least one hydroxyl group and optionally linked to the phenyl ring via a carbonyl, sulphone or sulphoxide group, at least one R group being an M.sub.1 moiety; with the proviso that where n is zero either at least one M.sub.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: March 16, 1999
    Assignee: Nycomed Imaging AS
    Inventors: Torsten Almen, Sven Andersson, Lars-Goran Wistrand, Klaes Golman, Oyvind Antonsen, Rune Fossheim, Unni Nordby Wiggen, Hakan Wikstrom, Tomas Klingstedt, Ib Luenbach, Arne Berg, Harald Dugstad
  • Patent number: 5808130
    Abstract: Relates to the direct esterification of phenols, particularly alkyl-substituted phenols, with a carboxylic acid or anhydride, in the presence of a strong acid catalyst. Also relates to the use of the acid anhydride to drive the esterification reaction to completion, where an initial reaction mixture has been formed using the carboxylic acid. Further relates to the achievement of economies in esterification by recovering dilute aqueous acid when either the acid or anhydride is used initially, for recycling to achieve economies of acid use.
    Type: Grant
    Filed: September 17, 1996
    Date of Patent: September 15, 1998
    Assignee: Henkel Corporation
    Inventor: Leroy Krbechek
  • Patent number: 5763681
    Abstract: A novel synthesis of compound having the formula: ##STR1## wherein T is a stabilizing spiro-linked polycycloalkylidene group, R.sup.3 is a C.sub.1 -C.sub.20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula:(R.sup.1 O).sub.3 Pwherein R.sup.1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula:R.sup.3 OHwherein R.sup.
    Type: Grant
    Filed: July 2, 1993
    Date of Patent: June 9, 1998
  • Patent number: 5756822
    Abstract: An acetamide derivative having the general formula (I): ##STR1## or a pharmacologically acceptable salt thereof; a synthetic intermediate of the above-mentioned acetamide derivative; a treating agent for peptic ulcer and for gastritis which comprises the above-mentioned compound having the general formula (I) as an effective ingredient, and a process for treating peptic ulcer and gastritis using the above-mentioned compound having the general formula (I), are disclosed.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: May 26, 1998
    Assignee: Kaken Pharmaceutical Co., Ltd.
    Inventors: Nobuo Ishiyama, Toshihiro Koyama, Mitsuo Hayashida, Katsuyuki Otsuka, Masahiro Fujii, Kunio Kimura, Yoshiyuki Hata, Nobuko Miyao
  • Patent number: 5734082
    Abstract: This invention relates to a class of aminimides structurally characterized as an acyl nitrogen-nitrogen ylide such that the acyl moiety possess the structural diversity element G, the quaternary nitrogen possess structural diversity elements E and F, and the quaternary nitrogen is bonded to a hydroxyethyl substituent, which in turn is bonded to an aminomethylene moiety that possess structural diversity elements A and B from the amino group and diversity element C from the methylene substituent, as shown below, ##STR1## wherein structural diversity element A, B, C, D, E, F and G are chosen from the set of elements consisting of substituted and unsubstituted as well as branched and straight chain alkyl, aryl, alkaryl, aralkyl, carbocyclic, heterocyclic, hydrogen, amino acid, peptide, polypeptide, protein, depsipeptide, carbohydrate derivatives, nucleotide derivatives, oligonucleotide derivatives, naturally occurring or synthetic organic structural motifs, reporter elements, organic moieties containing at least
    Type: Grant
    Filed: October 20, 1994
    Date of Patent: March 31, 1998
    Assignee: Arqule Inc.
    Inventors: Joseph C. Hogan, Jr., David Casebier, Paul S. Purth, Steve Gallion, Alan Kaplan
  • Patent number: 5710296
    Abstract: A method for preparing phenyl esters in high yields under mild reaction conditions is provided. Particularly preferred phenyl esters prepared in accordance with the inventive method are alkanyloxy-benzene compounds having a C.sub.2-18 alkyl. The method is practiced by reacting a carboxylic acid with an acid halide either in the presence of or followed by the addition of a phenol.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: January 20, 1998
    Assignee: The Clorox Company
    Inventors: LaFayette D. Foland, Thomas B. Ottoboni
  • Patent number: 5679833
    Abstract: Vinyl ester of an alcohol (such as benzoin) is made by reaction of the alcohol with a 3-haloalkyl acid halide (such as 3-chloropropional chloride or bromide) in an anhydrous liquid reaction medium comprising an aprotic solvent (such as toluene) and a hydrogen halide acceptor (such as a tertiary amine) at a temperature of at least 20.degree. C.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Allied Colloids Limited
    Inventors: Gerald Philip Benn, Janet Catrine Doyle, Peter Stuart Littlewood
  • Patent number: 5639907
    Abstract: A compound of the formula ##STR1##
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: June 17, 1997
  • Patent number: 5599974
    Abstract: Chemical compounds which interact inside the central water cavity of hemoglobin and bridge between the two .alpha. subunits can be used to allosterically modify hemoglobin towards tense and relaxed states. The functional groups employed are aldehydes and carboxylic acids, wherein the aldehydes form covalent bonds (schiff base) with amino acid residues of hemoglobin and the carboxylic acids form ionic bonds with amino acid residues of hemoglobin. Particularly useful compounds within the practice of this invention bond to the n-terminal valine of one .alpha. subunit of hemoglobin, and the lysine 99 and/or arginine 141 of the other .alpha. subunit.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: February 4, 1997
    Assignee: Center for Innovative Technology
    Inventors: Donald J. Abraham, Telih Boyiri, Martin Safo, Richmond Danso-Danquah
  • Patent number: 5597390
    Abstract: A di- or tri-ester polyether unsaturated acid amine reaction product effective as a fuel additive for reducing intake valve deposits and octane requirement increase, as well as controlling combustion chamber deposits, in gasoline engines is disclosed together with fuel compositions and methods of making and using the same. Also disclosed are compositions and methods for dispersing deposits in lubricating oil products.
    Type: Grant
    Filed: September 25, 1995
    Date of Patent: January 28, 1997
    Assignee: Ethyl Corporation
    Inventor: John T. Loper
  • Patent number: 5587509
    Abstract: A method of releasing a caged carboxylic acid in which a 2-alkoxy-5-nitro-phenyl photosensitive group blocks a carboxyl function and the compositions so produced are disclosed.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: December 24, 1996
    Assignee: Cornell Research Foundation, Inc.
    Inventors: George P. Hess, Barry K. Carpenter, Doraiswamy Ramesh, Raymond Wieboldt
  • Patent number: 5565605
    Abstract: A catalyst for producing an aryl ester, which includes a microporous material containing a metal element belonging to group IV, is described. This catalyst is insoluble and can be used as a heterogeneous catalyst, to produce an aryl ester in high yield with industrial advantages. In order to produce an aryl ester using the catalyst, a carbonate or an aliphatic carboxylate is transesterified with an aromatic hydroxy compound, or an aryl carboxylate is transesterified with a carbonate, or an alkyl aryl carbonate is disproportionated by transesterification.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: October 15, 1996
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hideaki Tsuneki, Masaru Kirishiki, Kenichi Watanabe, Yoshiyuki Onda
  • Patent number: 5563289
    Abstract: The present invention provides a unique and novel way of producing an acetoxystyrene. In this new process which comprises a single step, a mixture of (a) a carbinol, (b) an acetylating agent, and (c) an acid catalyst is dehydrated under suitable dehydration conditions of temperature and pressure to form said acetoxystyrene.
    Type: Grant
    Filed: October 13, 1995
    Date of Patent: October 8, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, Keith M. Russ
  • Patent number: 5552507
    Abstract: Diisocyanates containing carboxylic acid ester groups corresponding to the formula: ##STR1## in which R and R.sup.1 represent specified groups are produced by phosgenation of the corresponding diamines, optionally present in the form of an ammonium salt. These diisocyanates are useful as starting materials in the production of plastics containing urethane and/or urea groups and as starting materials for the production of intermediate products used for the production of such plastics.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: September 3, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Wamprecht, Klaus Jost, Stefan Penninger
  • Patent number: 5470878
    Abstract: Therapeutic compounds have the formula:(X)j-(non-cyclic core moiety),j being an integer from one to three, the core moiety is non-cyclic and X is a racemic mixture, R or S enantiomer, solvate, hydrate, or salt of: ##STR1## *C is a chiral carbon atom, n is an integer from one to four (preferably from one to three), one or more carbon atoms of (CH.sub.2).sub.n may be substituted by a keto or hydroxy group, and m is an integer from one to fourteen. Independently, R.sub.1 and R.sub.2 may be a hydrogen, a straight or branched chain alkane or alkene of up to twelve carbon atoms in length, or --(CH.sub.2).sub.w R.sub.5, w being an integer from two to fourteen and R.sub.5 being a mono-, di- or tri-substituted or unsubstituted aryl group, substituents on R.sub.5 being hydroxy, chloro, fluoro, bromo, or C.sub.1-6 alkoxy. Or jointly, R.sub.1 and R.sub.2 form a substituted or unsubstituted, saturated or unsaturated heterocyclic group having from four to eight carbon atoms, N being a hetero atom. R.sub.
    Type: Grant
    Filed: December 8, 1993
    Date of Patent: November 28, 1995
    Assignee: Cell Therapeutics, Inc.
    Inventors: John Michnick, Gail E. Underiner, J. Peter Klein, Glenn C. Rice
  • Patent number: 5463108
    Abstract: The present invention provides a unique and novel way of producing 4-acetoxystyrene. In this new process, 4-hydroxystyrene is acetylated, in the presence of an acetylation agent, under suitable conditions of temperature and pressure and for a sufficient period of time to form acetoxystyrene.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ, Lynn Massarelli
  • Patent number: 5430175
    Abstract: Caged carboxyl compounds in which a 2-alkoxy-5-nitrophenyl photosensitive group blocks a carboxyl function are disclosed. Preferably the compounds are neuroactive amino acids. The compounds are photolyzable by laser pulses at wavelengths above about nm within about 3 .mu.s and provide a product quantum yield of greater than about 0.2.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: July 4, 1995
    Assignee: Cornell Research Foundation, Inc.
    Inventors: George P. Hess, Barry K. Carpenter, Doraiswamy Ramesh, Raymond Wieboldt
  • Patent number: 5397802
    Abstract: Gem-Dichlorocyclopropanes (Analog II derivatives) which demonstrate antiproliferative activity toward MCF-7 cells, in vitro and are generally not reversed by estradiol or having intrinsic estrogenicity (except the hydroxyphenyl derivative Compound 30). In general the cyclopropane compounds have the formula: ##STR1## or any pharmaceutically acceptable salt thereof. X is selected from a group consisting of hydrogen and halogen atoms. The group R.sub.1 may be a hydrogen atom, an alkyl group, an acyl group, or an arylalkyl group. The group R.sub.2 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The group R.sub.3 may be a hydrogen atom, an alkyl group, a cycloalkyl group, a substituted aryl group or an unsubstituted aryl group. The group R.sub.4 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The R.sub.4 is absent when R.sub.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: March 14, 1995
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Robert A. Magarian, Joseph T. Pento, May T. Griffin
  • Patent number: 5391812
    Abstract: Polyglycolate compounds are provided having the general structure: ##STR1## wherein n is an integer from 2 to about 10; R is C.sub.1-20 linear or branched alkyl, alkoxylated alkyl, cycloalkyl, aryl, alkylaryl, substituted aryl; R' and R" are independently H, C.sub.1-20 alkyl, aryl, C.sub.1-20 alkylaryl, substituted aryl, and NR.sub.3.sup..alpha.+, wherein R.sup..alpha. is C.sub.1-30 alkyl; and L is a leaving group displaceable in a peroxygen bleaching solution by perhydroxide anion. When this compound is combined with a source of peroxygen in aqueous solution, then a plurality of stain removing peracids are formed. Such peracids are formed substantially sequentially beginning with the carbonyl adjacent to the leaving group L. Thus, a first stain removing peracid having the structure ##STR2## will be formed in amounts approaching quantitative yield.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: February 21, 1995
    Assignee: The Clorox Company
    Inventors: Richard R. Rowland, Ronald A. Fong, Richard J. Wiersema, Alfred G. Zielske
  • Patent number: 5384425
    Abstract: Diurea derivatives are provided which can be represented by the following general formula and salts thereof: ##STR1## wherein, R.sup.1 and R.sup.2 are the same or different, and each represents C.sup.1 -10 alkyl group, a C.sup.3 -18 cycloalkyl group, or a lower alkyl group substituted by cycloalkyl radical(s);R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different, and each represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, hydrocarbyl aralkyl group, a pyridyl group, or an unsubstituted or substituted phenyl group, the substituents of the phenyl group being selected from a group consisting of lower alkyl radical, halogen atom-substituted lower alkyl radical, halogen atom, nitro radical, amino radical, mono- or di-lower alkylamino radical, lower acylamino radical, hydroxyl radical, lower alkoxy radical and lower acyloxy radical;X represents an oxygen atom or a sulfur atom, and n.sup.1 and n.sup.2 represent an integer of 1 to 6; and wherein at least one of R.sup.3 -R.sup.
    Type: Grant
    Filed: October 7, 1993
    Date of Patent: January 24, 1995
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Noriki Ito, Tomoyuki Yasunaga, Yuichi Iizumi, Tomio Araki
  • Patent number: 5380918
    Abstract: 4-Acetoxystyrene of the formula I ##STR1## is prepared by a process in which a 1-(4-acetoxyphenyl)ethyl carboxylate of the formula II ##STR2## where R is C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, aryl or C.sub.7 -C.sub.10 -aralkyl, is converted in the presence of an acidic catalyst and of a polymerization inhibitor in an inert heat transfer medium at from 160.degree. to 250.degree. C. and from 0.1 to 300 mbar.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: January 10, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Brudermueller, Franz Merger
  • Patent number: 5354874
    Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: October 11, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5344963
    Abstract: A process for the production of substituted vinylbenzenes of the general formula: ##STR1## wherein R is a lower alkyl group having 1 to 4 C atoms, R.sub.1 is hydrogen or an acetyl group and R.sub.2 is hydrogen, a lower alkyl group having 1 to 4 C atoms or a benzyl group. A trialkylhydroquinone is cyclized with an aldehyde to an acetal and the latter is pyrolized to the end product. The substituted vinylbenzenes are valuable intermediate products in the synthesis of antioxidants.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: September 6, 1994
    Assignee: Lonza Ltd.
    Inventors: Aleksander Warm, David Laffan
  • Patent number: 5344952
    Abstract: A method for enzyme immunoassay for a ligand suspected to be present in a liquid sample includes signal amplification by use of at least two enzymes and a blocked modulator for one of the enzymes. Ligand present in the liquid binds to an antiligand and an enzyme-labeled tracer. The resulting bound fraction is separated and the enzyme in the tracer removes the blocking group from the blocked modulator. The modulator activates or inhibits a second enzyme which catalyzes the conversion of a substrate to a product. The presence or absence of the ligand in the liquid is indicated by a signal, such as a color change or a rate of color change, associated with the product. The invention includes a new class of enzyme inhibitors and blocked inhibitors and a kit of materials useful for performing the method of the invention.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Becton, Dickinson and Company
    Inventors: Patrick D. Mize, James P. O'Connell
  • Patent number: 5342985
    Abstract: The invention relates to a process for the metathesis of olefins which comprises reacting an olefin of the formula YCZ.dbd.CZ--(CX.sub.2).sub.n R.sup.2 (II) whereinn is an integer from 1 to 28,X represents H or F,Y represents H or alkyl having from 1 to 10 carbon atoms andZ represents H or a non-aromatic hydrocarbon group having from 1 to 6 carbon atoms and R.sup.2 represents H, alkyl, halogen, COOR.sup.3 or OR.sup.4, wherein R.sup.3 and R.sup.4 represent alkyl having from 1 to 15 carbon atoms or phenyl which is unsubstituted or contains from 1 to 3 substituents or wherein R.sup.4 is trialkylsilyl R.sup.5 Si, wherein R.sup.5 represents alkyl having from 1 to 5 carbon atoms, at a catalyst comprising an oxidic carrier charged with a rhenium compound as defined hereinbefore.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: August 30, 1994
    Assignee: Hoechst AG
    Inventors: Wolfgang A. Herrmann, Werner Wagner, Ursula Volkhardt
  • Patent number: 5283352
    Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 1, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
  • Patent number: 5279764
    Abstract: The invention relates to dihalogenobenzene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --R.sup.2wherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are as defined in the specification.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: January 18, 1994
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Georg Weber, Ulrich Finkenzeller, Andreas Wachtler, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
  • Patent number: 5274173
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: March 25, 1993
    Date of Patent: December 28, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5274175
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: December 28, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5274174
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: December 28, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5247124
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: August 25, 1992
    Date of Patent: September 21, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5245074
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: May 21, 1992
    Date of Patent: September 14, 1993
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5240625
    Abstract: A lubricating oil additive suitable as an extreme pressure/anti-wear additive comprises the product obtainable by reacting at elevated temperature a mixture comprising (i) sulphur, (ii) at least one C.sub.10 to C.sub.100 unsaturated carboxylic acid, and (iii) at least one hydrocarbyl-substituted phenol, the amount of (iii) in the mixture being 15 to 65% w/w based on the combined weight of (i) (ii) and (iii). The reaction mixture can further comprise an olefin and/or, a mercaptan and/or a lubricating oil as a diluent. The additive is also useful as an anti-oxidant. Additive concentrates and lubricating oil compositions comprise a lubricating oil and the additives of the present invention.
    Type: Grant
    Filed: March 20, 1990
    Date of Patent: August 31, 1993
    Assignee: BP Chemicals (Additives) Limited
    Inventor: Sean P. O'Connor
  • Patent number: 5208224
    Abstract: Novel phosphorus containing compounds are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful in preventing the intestinal absorption of cholesterol and thus are useful in the treatment of hypercholesterolemia and atherosclerosis.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: May 4, 1993
    Assignee: Warner-Lambert Company
    Inventors: Gary L. Bolton, Janak K. Padia, Bharat K. Trivedi
  • Patent number: 5198568
    Abstract: This invention relates to novel compositions of matter which are esters with enhanced water solubility, for use in aqueous enzymatic resolution reactions of racemic mixtures of these esters for producing the separate chiral isomers of the racemic mixture. The invention also relates to novel methods for preparing these esters. The importance of the production of the separate chiral isomers of the racemic mixtures resides in the isolation of the isomers which frequently have different biological activities. Of particular significance regarding the water soluble esters of this invention is that they are derivatized with groups which enhance their aqueous solubility and their reactivity with enzymatic resolving methods which are mediated in an aqueous environment.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: March 30, 1993
    Assignee: Sepracor, Inc.
    Inventors: Charles M. Zepp, Stephen A. Wald, David R. Dodds
  • Patent number: 5194672
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5171915
    Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine