Acyclic Polycarbon Hydrocarbyl Group Bonded Directly To The Benzene Group Patents (Class 568/766)
-
Patent number: 11795128Abstract: Disclosed are methods for preparing cannabigerol (CBG) or a CBG analog, embodiments of the method comprising providing a compound (I); combining the compound (I) with geraniol and a solvent to form a reaction mixture; and combining the reaction mixture with an acid catalyst to form a product mixture comprising the CBG or the CBG homolog. The method may further comprise separating the CBG or the CBG analog from the product mixture and may further comprise purifying the CBG or CBG analog. Methods for preparing cannabigerolic acid (CBGA) or a cannabigerolic acid analog are also disclosed. The present disclosure also provides highly purity CBG, CBGA, and analogs thereof.Type: GrantFiled: August 8, 2022Date of Patent: October 24, 2023Inventors: Daniel Brumar, Mahmood Azizpour Fard, Ben Geiling, Mohammadmehdi Haghdoost Manjili
-
Patent number: 11643380Abstract: Disclosed are methods for preparing cannabigerol (CBG) or a CBG analog, embodiments of the method comprising providing a compound (I); combining the compound (I) with geraniol and a solvent to form a reaction mixture; and combining the reaction mixture with an acid catalyst to form a product mixture comprising the CBG or the CBG homolog. The method may further comprise separating the CBG or the CBG analog from the product mixture and may further comprise purifying the CBG or CBG analog. Methods for preparing cannabigerolic acid (CBGA) or a cannabigerolic acid analog are also disclosed. The present disclosure also provides highly purity CBG, CBGA, and analogs thereof.Type: GrantFiled: March 21, 2022Date of Patent: May 9, 2023Inventors: Daniel Brumar, Mahmood Azizpour Fard, Ben Geiling, Mohammadmehdi Haghdoost Manjili
-
Patent number: 10644342Abstract: Flow batteries and other electrochemical systems can contain an active material that is a coordination complex having at least one monosulfonated catecholate ligand or a salt thereof bound to a metal center. The monosulfonated catecholate ligand has a structure of More particularly, the coordination complex can be a titanium coordination complex with a formula of DgTi(L1)(L2)(L3), in which D is a counterion selected from H, NH4+, Li+, Na+, K+, or any combination thereof g ranges between 3 and 6; and L1, L2 and L3 are ligands, where at least one of L1, L2 and L3 is a monosulfonated catecholate ligand. Methods for synthesizing such monosulfonated catecholate ligands can include providing a neat mixture of catechol and up to about 1.3 stoichiometric equivalents of sulfuric acid, and heating the neat mixture at a temperature of about 80° C. or above to form 3,4-dihydroxybenzenesulfonic acid or a salt thereof.Type: GrantFiled: March 3, 2016Date of Patent: May 5, 2020Assignee: Lockheed Martin Energy, LLCInventors: Scott Thomas Humbarger, Matthew Millard
-
Patent number: 10316047Abstract: Coordination complexes can have a metal center with at least one unsubstituted catecholate ligand and at least one monosulfonated catecholate ligand or a salt thereof bound thereto. Some coordination complexes can have a formula of DgTi(L1)x(L2)y, in which D is a counterion selected from NH4+, Li+, Na+, K+, or any combination thereof; g ranges between 2 and 6; L1 is an unsubstituted catecholate ligand; L2 is a monosulfonated catecholate ligand; and x and y are non-zero numbers such that x+y=3. Methods for synthesizing such coordination complexes can include providing a neat mixture of catechol and a sub-stoichiometric amount of sulfuric acid, heating the neat mixture to form a reaction product containing catechol and a monosulfonated catechol or a salt thereof, and forming a coordination complex from the reaction product without separating the catechol and the monosulfonated catechol or the salt thereof from one another.Type: GrantFiled: March 3, 2016Date of Patent: June 11, 2019Assignee: Lockheed Martin Energy, LLCInventors: Scott Thomas Humbarger, Matthew Millard
-
Patent number: 9227090Abstract: Skin lightening additives and skin lightening compositions having at least one of a heterosubstituted, saturated or unsaturated aliphatic acid are described. The compositions are suitable for topical application and may comprise 12-hydroxystearic acid, ricinoleic acid or both.Type: GrantFiled: October 20, 2010Date of Patent: January 5, 2016Assignee: Conopco, Inc.Inventor: Stephen Alan Madison
-
Patent number: 8981163Abstract: Disclosed is a fluorine-containing aromatic compound represented by the following general formula (1) and its production method. In the formula (1), R1 is a hydroxyl group or amino group, each of R2 to R5 is independently a hydrogen atom, or a C1-4 straight chain or a C3 or C4 branched chain alkyl group, hydrogen atoms of the alkyl group may partially or totally be replaced with fluorine atoms, n is an integer of 0 to 2, and each of m and l is independently 0 or 1. A polymer derived from this fluorine-containing aromatic compound contains —C(CF3)2OH group at a position away from the polymer main chain. Therefore, it is useful for resist use.Type: GrantFiled: August 8, 2012Date of Patent: March 17, 2015Assignee: Centrall Glass Company, LimitedInventors: Junya Nakatsuji, Makoto Matsuura, Kazuhiro Yamanaka
-
Publication number: 20140243424Abstract: Methods of treating or suppressing oxidative stress disorders affecting normal electron flow in the cells, including mitochondrial diseases, impaired energy processing disorders, neurodegenerative diseases, diseases of aging and diseases caused by reactive oxygen species are disclosed, as well as compounds useful in the methods of the invention, such as such as catechol or ortho-quinone derivatives of Formula (I).Type: ApplicationFiled: June 14, 2012Publication date: August 28, 2014Applicant: Edison Pharmaceuticals, Inc.Inventors: Paul Mollard, Gloria Pfister
-
Publication number: 20140227239Abstract: It is an object of the present invention to provide a growth hormone secretagogue that is excellent in effect of promoting secretion of a growth hormone and is orally available. The growth hormone secretagogue of the present invention contains one or more selected from the group consisting of S-adenosylmethionine and/or a salt thereof, a Siberian larch extract, an olive extract, and a stilbene-based compound as an active ingredient. S-adenosylmethionine and/or the salt thereof may be a form itself of chemically synthesized S-adenosylmethionine and/or the salt thereof, or may be a microbial cell or a culture containing S-adenosylmethionine and/or the salt thereof. The stilbene-based compound may be an extract extracted from a Vitaceae plant or a Gnetaceae plant. The olive extract may be an extract separated from a fruit of olive.Type: ApplicationFiled: March 2, 2012Publication date: August 14, 2014Applicant: LION CORPORATIONInventors: Toshio Gokita, Ikuko Kamada, Kiwamu Suzuki, Hiroaki Kambayashi
-
Publication number: 20140206905Abstract: The present invention relates to a process of preparing tocotrienol quinones. It has been found that this process allows the formation of the R-isomer in a high yield in a very efficient and economically interesting way. Said process is particularly useful when implemented in an industrial process. Furthermore, it has been found that this process allows using isomer mixtures as they result from traditional industrial synthesis.Type: ApplicationFiled: September 21, 2012Publication date: July 24, 2014Applicant: SAM IP ASSETS B.V.Inventors: Gerhard Schiefer, Thomas Netscher, Alexander Lucia Leonardus Duchateau
-
Publication number: 20140155339Abstract: Compositions comprising hydroxytyrosol-containing formulations and treatment regiments comprising hydroxytyrosol and/or oleuropein and chemotherapeutic agents are disclosed. Compositions and/or regiments may optionally include the administration of vitamins, minerals, and anti-oxidants. Methods for using these compositions and treatment regimens for treating subjects for diseases, such as a malignancy, and for inducing or enhancing angiogenesis, treating or preventing oxidative stress, for treating or preventing high glucose-induced dysfunction, treating or preventing chemotherapy-induced dysfunction, and for improving cell viability are provided. Various methods for use of the hydroxytyrosol compositions for inhibition of lysine specific demethylase 1 (LSD1) in various cancers are also provided.Type: ApplicationFiled: November 27, 2013Publication date: June 5, 2014Inventors: Darlene E. McCord, Thomas Karagiannis
-
Publication number: 20130150607Abstract: This invention is directed to a new process for making an alkylaromatic compound. In an embodiment of this invention, the process is directed to selective synthesizing an alkylaromatic compound comprising a high amount of dialkylate product. In general, this process involves contacting at least one alkylatable aromatic compound with an alkylating agent and a catalyst under suitable reaction conditions such that the resulting reactor effluent prior to any stripping step may be characterized by a dialkylate product content of at least 44 wt % and a trialkylate and higher polyalkylate product content of no more than 20 wt %. The alkylaromatic compounds produced have excellent thermal and oxidative stabilities, good additive solvency, and improved seal compatibility while maintaining good VI and low temperature properties. They are useful as lubricant basestocks and lubricant additives.Type: ApplicationFiled: December 7, 2011Publication date: June 13, 2013Inventor: Beth A. WINSETT
-
Publication number: 20130150608Abstract: This invention is directed to an improvement in the process for the production of alkylaromatic compounds that results in lower levels of residual unreacted materials in the final product. This invention comprises: 1) alkylation of an aromatic compound with an alkylating agent and a catalyst to produce an effluent stream comprising an alkylaromatic compound and unreacted materials; 2) heating the effluent stream; 3) stripping the effluent stream in a stripping device in the presence of steam; 4) separating a stripping stream from the stripping device, the stripping stream rich in unreacted materials; and 5) separating a product stream from the stripping device, the product stream rich in alkylated aromatic compound.Type: ApplicationFiled: December 13, 2011Publication date: June 13, 2013Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
-
Publication number: 20130053450Abstract: Methods of treating or suppressing pervasive developmental disorders (PDDs) including; autistic disorder, Asperger's syndrome, childhood disintegrative disorder (CDD), Rett's disorder, and PDD-not otherwise specified (PDD-NOS) or attention deficit/hyperactivity disorder (ADHD) comprising administering to a subject in need thereof a therapeutically effective amount of one or more compounds as disclosed herein.Type: ApplicationFiled: October 12, 2012Publication date: February 28, 2013Applicant: EDISON PHARMACEUTICALS, INC.Inventor: EDISON PHARMACEUTICALS, INC.
-
Publication number: 20120302645Abstract: The use of hydroxytyrosol or an olive juice extract containing hydroxytyrosol for improving muscle differentiation and thus improving or maintaining the body's adaptation to exercise is disclosed. The pharmaceutical and nutraceutical compositions comprising hydroxytyrosol useful for conditions characterized by altered muscle differentiation especially under inflammatory conditions, such as delayed onset muscle soreness subsequent to strenuous exercise or sarcopenia are provided.Type: ApplicationFiled: October 8, 2010Publication date: November 29, 2012Inventors: Jiankang Liu, Ying Wang-Schmidt, Karin Wertz, Zhihui Feng
-
Publication number: 20120259020Abstract: Transdermal therapeutic systems that contain 4-n-butylresorcinol as an active ingredient.Type: ApplicationFiled: July 14, 2010Publication date: October 11, 2012Applicant: Beiersdorf AGInventors: Karl-Heinz Woeller, Ludger Kolbe, Cathrin Scherner, Rainer Wolber
-
Publication number: 20120184782Abstract: A heparanase activity inhibitor containing, as an active ingredient, a 4-alkylresorcinol represented by formula (I): wherein R represents a C1-6 linear or branched alkyl group.Type: ApplicationFiled: September 29, 2010Publication date: July 19, 2012Inventors: Shunsuke Iriyama, Hirotada Fukunishi, Masaru Suetsugu, Satoshi Amano
-
Patent number: 8207380Abstract: An alkylated hydroxyaromatic compound prepared by reacting at least one hydroxyaromatic compound with a branched olefinic oligomer having from about 20 to about 80 carbon atoms in the presence of a acid catalyst. The alkylated hydroxyaromatic compound has been determined to be substantially free of endocrine disruptive chemicals when the effects were quantified on pubertal development and thyroid function in the intact juvenile female rat.Type: GrantFiled: April 27, 2007Date of Patent: June 26, 2012Assignee: Chevron Oronite LLCInventors: Curt B. Campbell, James J. Harrison
-
Publication number: 20120142786Abstract: Oregano extract can act as a stimulant, yet it does not interfere with sleep patterns or induce nervousness the way many stimulants such as caffeine can. It also has the benefits of promoting improved vigilance, improving attention and ability to focus on a task, and improving general alertness.Type: ApplicationFiled: February 19, 2010Publication date: June 7, 2012Inventors: Regina Goralczyk, Jonas Wittwer, Hasan Mohajeri
-
Publication number: 20120127633Abstract: A metal electrolytic capacitor capable of quickly absorbing and immobilizing a belching vapor of a driving electrolyte and widely reducing leakage when an explosion-proof valve operates. An aluminum electrolytic capacitor body is configured by housing a capacitor element in a cylindrical aluminum case, a pair of leads extend from the capacitor body, an explosion-proof valve is formed on a top panel portion of the metal case, a cylindrical cap as a casing is attached from above to the capacitor body, a plurality of small openings are formed on a top panel portion (bottom portion) of the cap, and an absorbent or a mixture of an absorbent and a water molecular compound wrapped in a permeable fiber material, such as unwoven fabric and filter paper, is placed in a space between the cap and the top panel portion of the capacitor body.Type: ApplicationFiled: June 2, 2010Publication date: May 24, 2012Inventors: Koichi Mori, Mitsuru Nozue, Minoru Yagi
-
Publication number: 20120052141Abstract: The present invention is directed inter alia to the use of at least one compound selected from the group consisting of (?)-epigallocatechin gallate, resveratrol, eicosapentaenoic acid, docosahexaenoic acid, rose hip extract/concentrate, hydroxytyrosol, lycopene, lutein, ?-cryptoxanthin, zeaxanthin and derivatives thereof, for the treatment of cellulite, for the prevention of the development of mild cellulite, for the prevention of the progression of mild cellulite to severe cellulite, for smoothening the micro relief of the skin, for maintaining or increasing the tensile properties of the skin, and/or for reducing the fat mass and the circumference at the hips and thighs, as well as to the corresponding cosmetic and medical methods.Type: ApplicationFiled: November 4, 2011Publication date: March 1, 2012Applicant: DSM IP ASSETS B.V.Inventors: Regina GORALCZYK, Joseph Schwager, Karin Wertz
-
Publication number: 20100331377Abstract: The present disclosure relates to compositions for and methods of repairing the stratum corneum, compositions and methods for inhibiting excessive transepidermal water loss, compositions for and methods of treating skin that is distressed or wounded as a result of a disease or other biological condition or process (as distinguished from wounds resulting from trauma), compositions for and methods of treating chronic wounds, and compositions for the inhibition and treatment of necrosis and extended quiescence that result in cellular necrosis instead of normal proliferationType: ApplicationFiled: June 25, 2010Publication date: December 30, 2010Inventor: Darlene McCord
-
Publication number: 20100292345Abstract: The present invention relates to the use of the cannabinoid cannabigerol (CBG) in the manufacture of medicaments for use in the treatment of diseases and conditions benefiting from concurrent agonism of the CBi and the CB2 cannabinoid receptors. Such diseases or conditions to be treated are taken from the group: pain, neurodegenerative disease, ischemic disease, brain injury or damage, acquired brain injury, age related inflammatory or autoimmune disease, cachexia, nausea and vomiting, glaucoma, movement disorders, rheumatoid arthritis, asthma, allergy, psoriasis, Crohn's disease, systemic lupus erythematosus, diabetes, cancer, osteoporosis, renal ischemia and nephritis.Type: ApplicationFiled: June 25, 2008Publication date: November 18, 2010Applicant: GW PHARMA LIMITEDInventor: Roger Pertwee
-
Patent number: 7759527Abstract: The invention entitled “A Microwave Induced One Pot Process for The Preparation of Arylethenes” provides a method for the preparation of commercially important 2- or 4-hydroxy substituted arylethenes like styrenes or stilbenes in one pot utilizing cheaper substrates in the form of 2- or 4-hydroxy substituted cinnamic acids and their derivatives as well as reagents in the form of base such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, ammonium acetate, imidazole, methylimidazole and the combination thereof, with or without solvent such as dimethylformamide, dimethylsulfoxide, ethylene glycol, diethylene glycol, acetonitrile, acetone, methyl imidazoles, ionic liquid, water and the like. The reaction time vary from 1 min-12 hrs and yield of the products from 49-76% depending upon the base, acid, substrate source of heating monomode or multimode microwave or conventional.Type: GrantFiled: March 27, 2007Date of Patent: July 20, 2010Assignee: Council of Scientific & Industrial ResearchInventors: Arun Kumar Sinha, Anuj A Sharma, Vinod Kumar
-
Publication number: 20100168229Abstract: A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.Type: ApplicationFiled: December 17, 2009Publication date: July 1, 2010Inventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
-
Publication number: 20100168448Abstract: The invention relates to methods of preparing cannabinoids in substantially pure form starting from plant material. Also described are substantially pure preparations of various cannabinoids and cannabinoid acids, and also extracts enriched in cannabinoids and cannabinoid acids.Type: ApplicationFiled: March 1, 2010Publication date: July 1, 2010Applicant: GW Pharma LimitedInventors: Ian Flockhart, Gary William Wheatley, Su Dring, Leslie Archer
-
Publication number: 20100028318Abstract: The present invention has its object to provide a safer and highly effective composition capable of relieving or preventing xerostomia. The present invention relates to an agent for relieving or preventing xerostomia comprising an oxidized coenzyme Q and/or a reduced coenzyme Q as active ingredients, a composition containing the agent for relieving or preventing xerostomia in a form of a food product, a health food, a dietary supplement, a supplement, an oral health care product, a medicament, a quasi drug, a pet food, a feed or the like, and a method for treating xerostomia and a method for reducing risks of xerostomia comprising administering the composition.Type: ApplicationFiled: January 31, 2008Publication date: February 4, 2010Applicants: KANEKA CORPORATIONInventors: Ichiro Saito, Kenji Fujii, Kazuya Hamada
-
Patent number: 7402713Abstract: Tyrosine was converted to p-hydroxystyrene in a two-step reaction without purification of individual intermediates. Conditions were determined for bromination of tyrosine in which reactive intermediates were formed. The mixture of these intermediates was used directly in a second step reaction to produce p-hydroxystyrene. The p-hydroxystyrene was further acetylated to produce p-acetoxystyrene in the second step reaction vessel.Type: GrantFiled: March 7, 2006Date of Patent: July 22, 2008Assignee: E.I. du Pont de Nemours and CompanyInventors: Steven W. Shuey, Mukesh C. Shah
-
Patent number: 7355063Abstract: The compound represented by the following formula (1): wherein A, B, R1, R2, R3 and Z are as defined in the specification is analogous to shogaol and gingerol useful in the fields of foods, medicines, quasi-drugs, cosmetics, etc., and more highly active in tyrosinase activity inhibition, etc. than shogaol and gingerol.Type: GrantFiled: March 26, 2004Date of Patent: April 8, 2008Assignee: Toagosei Co., Ltd.Inventors: Shuhei Yamaguchi, Hisatoyo Kato
-
Patent number: 7112705Abstract: The present invention relates to a process for the preparation of alkylated dihydroxybenzene by alkylating dihydroxy benzene with tertiary butyl alcohol in the presence of a solid acid/solid polymer catalyst.Type: GrantFiled: December 26, 2001Date of Patent: September 26, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Narayanan Sankarasubbier, Palaniappan Srinivasan, Katravulapalli Veera Venkata Satya Bhaskara Sita Rama Murthy
-
Patent number: 6911562Abstract: A process for the preparation of a compound of formula I: wherein R is a hydrogen or a C1-6 alkyl group which is straight chain, branched or cyclic, with or without an oxygen, nitrogen or sulphur heteroatom anywhere in the chain or ring by reacting a compound of formula II: with a source of hydrogen selected from either hydrogen or water in the presence of a mixture of at least two catalysts selected from nickel, raney nickel, and palladium, at a pH below 7.0 in a solvent medium comprising an alcohol having a carbon chain length of up to 3.Type: GrantFiled: July 8, 2004Date of Patent: June 28, 2005Assignee: Unilever Home & Personal Care USA division of Conopco, Inc.Inventors: Ramachandra Bhat, Vinodkumar Ramniranjan Dhanuka, Bijan Harichian
-
Patent number: 6806395Abstract: A process for producing a 3,5-bisalkylphenol (2) according to the following reaction scheme: (wherein R1 represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, or a hydroxyl-protecting group (other than methyl group); R2 represents a C1 to C5 lower alkyl group or an optionally substituted phenyl group; and each of R3 and R4, which may be identical to or different from each other, represents a lower alkyl group, an aralkyl group, or an aryl group); a carbinol compound (1); and a process for producing the carbinol compound. The production process of the present invention enables efficient and safe production of a variety of 3,5-bisalkylphenols including 3,5-diisopropylphenol, which are important as synthesis intermediates for drugs and agricultural chemicals, in shorter steps at high purity in high yield, thus contributing to consistent supply of drugs and agricultural chemicals.Type: GrantFiled: March 18, 2003Date of Patent: October 19, 2004Assignee: Kowa Co., Ltd.Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
-
Publication number: 20040110847Abstract: The present invention relates to new antioxidative and cytotoxic hydroquinone compounds 10′(Z),13′(E),15′(E)-heptadecatrienylhydroquinone (1) and 10′(Z),13′(E)-heptadecadienylhydroquinone (2) that were mainly isolated from an ethanol extract of the sap of Rhus succedanea. The structures of these compounds were determined by spectral analyses and showed potent antioxidative activity and cytotoxicity against human cancer cells. This invention also includes anti-tumor pharmaceutical composition of the hydroquinone compounds.Type: ApplicationFiled: June 11, 2002Publication date: June 10, 2004Inventors: Pei-Lin Wu, Shwu-Bin Lin, Robin Yih-Yuan Chiou
-
Patent number: 6717020Abstract: Disclosed are a method of producing p-hydroxyphenylalkanol of formula(I): wherein R1 and R2 independently represent hydrogen, an alkyl or a phenyl which may be substituted with an alkyl, or the like, R3, R4, R5, R6 and R7 independently represent hydrogen, an alkyl or the like and n denotes an integer from 0 to 7, the method being characterized in that a phenol compound of formula (II): wherein R1 and R2 respectively represent the aforementioned meaning, is reacted with an unsaturated alcohol of formula (III): R3R4C═C(R5)—C(R6)(R7)—(CH2)n—OH (III) wherein R3, R4, R5, R6, R7 and n respectively represent the same as defined above, in the presence of (A) at least one compound selected from the group consisting of alkali metals, alkali metal compounds, alkaline earth metals and alkaline earth metal compounds and (B) at least one compound selected from the group consisting of transition metals and transition metal compounds, and the like.Type: GrantFiled: March 27, 2003Date of Patent: April 6, 2004Assignee: Sumitomo Chemical Company, LimitedInventor: Chikara Murakami
-
Patent number: 6670513Abstract: An alkylated hydroxyl-containing aromatic compound is produced by isomerizing a normal alpha-olefin having from about 16 to about 30 carbon atoms in the presence of a first solid, acidic catalyst capable of inducing both olefin isomerization and skeletal isomerization to produce a mixture of isomerized olefin, then alkylating an hydroxyl-containing aromatic compound with the mixture of isomerized olefins in the presence of a second solid, acidic catalyst. The first solid, acidic catalyst can be SM-3, MAPO-11, SAPO-11, SSZ-32, ZSM-23, MAPO-39, SAPO-39, ZSM-22, SSZ-20, ZSM-35, SUZ-4, NU-23, NU-87, natural ferrierite or synthetic ferrierite. The second solid, acidic catalyst can be a sulfonic acid anionic ion exchange resin catalyst or an acidic clay.Type: GrantFiled: December 3, 1999Date of Patent: December 30, 2003Assignees: Chevron Oronite Company, LLC, Chevron Oronite S.A.Inventors: Curtis Bay Campbell, Jean Louis Le Coënt
-
Patent number: 6451879Abstract: A process for producing a phenolic resin of good hue, characterized by reacting a hydroxylated aromatic compound with an unsaturated cyclic hydrocarbon compound in the presence of both active hydrogen and a reducing metal compound with the aid of an acid catalyst, subsequently deactivating the catalyst, and then removing the catalyst, the metal compound, and the starting materials remaining unreacted; and a process for producing an epoxy resin which comprises a step of reacting the phenolic resin with an epihalohydrin. By these processes, a phenolic resin and an epoxy resin are obtained which each is colored little and has an excellent hue. These resins are useful as resins for electrically insulating materials, especially as resins for semiconductor encapsulation materials and for laminated plates.Type: GrantFiled: April 13, 2001Date of Patent: September 17, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Satoshi Mori, Fumiaki Oshimi, Ryuichi Ueno
-
Patent number: 6407150Abstract: A process for producing phenol resin having good color tone, which process comprises reacting hydroxyl group-containing aromatic compound and unsaturated cyclic hydrocarbon under the condition that the moisture is 100 ppm or less and the concentration of Friedel-Crafts catalyst is 0.07 mass % or less in a reaction system and a process for producing epoxy resin having good color tone, which process comprises reacting the obtained phenol resin and epihalohydrin in the presence of base catalyst, removing remaining catalyst and further removing unreacted epihalohydrin.Type: GrantFiled: August 10, 2000Date of Patent: June 18, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Satoshi Mori, Fumiaki Oshimi, Masato Hattori
-
Publication number: 20020058848Abstract: A process for producing an aromatic hydroxyl compound alkylated at the ortho position in high yield by subjecting an aromatic hydroxyl compound and-an alkyl alcohol to a gas phase catalytic reaction in the presence of a metal oxide catalyst. The aromatic hydroxyl compound is a mixture of a phenol and ortho cresol, and the amount of ortho cresol in the mixture is 0.6 mole or less per 1 mole of phenol.Type: ApplicationFiled: September 10, 2001Publication date: May 16, 2002Inventors: Hitoshi Ota, Masaru Aga
-
Publication number: 20010025126Abstract: The isomerization of an alkylated phenol composition that contains an ortho-alkyl substituted phenol component to isomerize and reduce the level of ortho-alkyl substituted phenol component therein can be accomplished by heating that composition in the presence of a catalytically effective amount of a solid acid catalyst to carry out such isomerization and reduction in the level of ortho-alkyl substituted phenol. Examples of suitable solid acid catalysts can be selected from the H-form zeolites, the supported sulfonic acids, and the heteropoly acids. The resulting isomerized product can be subsequently phosphorylated.Type: ApplicationFiled: April 26, 2001Publication date: September 27, 2001Inventors: Anantha N. Desikan, George E. Whitwell
-
Patent number: 6255538Abstract: Disclosed is a process for the preparation of dialkyl aromatic hydroxyl compounds such as dialkylphenols, dialkylbenzenediols, dialkylnaphthols and dialkylnaphthalenediols, especially 2,5-dialkylhydroquinone, by contacting an aromatic hydroxy compound with an olefin in the presence of a sulfonic acid and sulfuric acid.Type: GrantFiled: January 5, 2000Date of Patent: July 3, 2001Assignee: Eastman Chemical CompanyInventors: Shawn Marie Dougherty, Sharon Denise DeBord, Robert Joseph Maleski
-
Patent number: 6013844Abstract: A process for preparing catechol monoethers or catechols of the formula Ia or Ib ##STR1## where R.sup.1 and R.sup.2 are, independently of one another, hydrogen or C.sub.1 -C.sub.8 hydrocarbon radicals, and R.sup.3 is a C.sub.1 -C.sub.8 hydrocarbon radical, which comprises a 2-hydroxycyclohexanone dialkyl ketal of the formula II or a 2-alkoxycyclohexanone of the formula III ##STR2## a) being reacted in the gas phase in the presence of palladium on zirconium oxide as catalyst to obtain compounds Ia orb) carrying out stage a) in the presence of water to obtain compounds Ib.Type: GrantFiled: July 15, 1998Date of Patent: January 11, 2000Assignee: BASF AktiengesellschaftInventors: Daniel Heineke, Uwe Dingerdissen, Joachim Wulff-Doring, Michael Hesse
-
Patent number: 5712231Abstract: The present invention provides novel polymers comprising a plurality of dihydroxy aromatic moieties and at least one polyalkyl moiety. In one embodiment of the present invention, the polymer is formed from about 2 to about 50 interconnected dihydroxy aromatic moieties each having an attached polyalkyl moiety. In another embodiment of the present invention, the polymer is represented by the formula A.sub.x P.sub.y where A is an aromatic dihydroxy moiety and P is a polyalkyl moiety. The polymers of the invention are useful as lubricating oil additives.Type: GrantFiled: June 4, 1996Date of Patent: January 27, 1998Assignee: Exxon Research and Engineering CompanyInventors: Abhimanyn Onkar Patil, Manuel Anthony Francisco, Ken Lewtas, Howard Lih Fang
-
Patent number: 5663457Abstract: Conventional low vinylidene polyolefins are condensed with hydroxyaromatics under the influence of macroreticular ion exchange resins in acid form to yield alkylated hydroxyaromatics.Type: GrantFiled: February 16, 1996Date of Patent: September 2, 1997Assignee: The Lubrizol CorporationInventor: Christopher Jay Kolp
-
Patent number: 5543487Abstract: A hydroxymethylated resorcinol coupling agent is provided, including a hydroxymethylated resorcinol as an active ingredient, which enables commercial thermosetting adhesives such as bisphenol-A epoxy, phenol-resorcinol-formaldehyde, emulsion-polymer isocyanate, phenol-formaldehyde, resorcinol-formaldehyde and other resins of similar chemical nature to develop strong and durable bonds to a variety of untreated and preservatively treated woods. The resulting bonds to wood withstand delaminating stresses that occur with weather and water in exterior environments.Type: GrantFiled: November 22, 1994Date of Patent: August 6, 1996Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Charles B. Vick, Klaus H. Richter, Bryan H. River
-
Patent number: 5510402Abstract: The novel compounds of the formula I ##STR1## in which n is an integer from the range from 4 to 8 and m is an integer from the range from 1 to 4,A is the aliphatic, aromatic, araliphatic or heterocyclic radical of a monobasic to tetrabasic carboxylic acid, andR.sup.1 and R.sup.1', independently of one another, are C.sub.1 -C.sub.24 alkyl or C.sub.5 -C.sub.8 cycloalkyl, are suitable for stabilizing organic material against thermal, oxidative or actinic degradation.Type: GrantFiled: November 24, 1993Date of Patent: April 23, 1996Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Rita Pitteloud
-
Patent number: 5508275Abstract: Lipid-selective antioxidants of the formula I(A).sub.a (L)(X).sub.a, (I),in whichA=an antioxidative component,L=a bridging member,X=a lipophilic componenta and a'=independently of one another the numbers 1 or 2.The compounds are used for the protection of lipid-containing substances against oxidation and in pharmaceuticals for the prophylaxis and treatment of diseases in which bioradicals are involved, in particular of coronary, circulatory and vascular diseases.Type: GrantFiled: March 15, 1994Date of Patent: April 16, 1996Assignee: Hoechst AktiengesellschaftInventors: Klaus-Ulrich Weithmann, Gunther Wess, Dirk Seiffge
-
Patent number: 5420363Abstract: An optically active tri-substituted methane compound having, as substituents, an aromatic ring group and a phenyl group having hydroxyl group at ortho or para position can be obtained by allowing a phenol compound unsubstituted at the ortho- or/and para-position to react with an optically active secondary carbinol compound having an aromatic ring group at the alpha-position in the presence of tri-substituted phosphine and diazodicarboxylate or diazodicarboxamide. These and other optically active tri-substituted methane compounds are useful as active ingredients for medicines or as intermediate compounds for preparing medicines.Type: GrantFiled: June 27, 1994Date of Patent: May 30, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuru Shiraishi, Shoji Fukumoto
-
Patent number: 5414153Abstract: Phenolic compounds, e.g., the phenols and phenol ethers, are selectively hydroxylated whereby the amounts of the final product para isomer are enhanced, for example in favor of hydroquinone versus pyrocatechol in the event of the hydroxylation of phenol, by reacting such phenolic compounds with hydrogen peroxide, advantageously in a polar, aprotic, organic solvent reaction medium, in the presence of a catalytically effective amount of a sulfonated polymer and a cocatalytically effective amount of an aromatic ketone compound.Type: GrantFiled: April 5, 1993Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
-
Patent number: 5399785Abstract: Disclosed is a chemically stable tyrosinase activity inhibitor having high tyrosinase activity inhibition effect and low toxicity. The tyrosinase activity inhibitor has a structure of the formula: ##STR1## wherein R.sub.1, R.sub.3 and R.sub.4 are a hydrogen atom or an alkyl or alkenyl group having 1 to 9 carbon atoms, and R.sub.2 is an alkyl or alkenyl group having 2 to 9 carbon atoms.Type: GrantFiled: August 4, 1993Date of Patent: March 21, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Yasutaka Miura, Yasuhiro Kinoshita, Yoshikazu Yamamoto, Kunio Takahashi, Kiyotaka Koyama, Kaoru Takatori
-
Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
-
Patent number: 5354913Abstract: An optically active tri-substituted methane compound having, as substituents, an aromatic ring group and a phenyl group having hydroxyl group at ortho or para position can be obtained by allowing a phenol compound unsubstituted at the ortho- or/and para-position to react with an optically active secondary carbinol compound having an aromatic ring group at the alpha-position in the presence of tri-substituted phosphine and diazodicarboxylate or diazodicarboxamide. These and other optically active tri-substituted methane compounds are useful as active ingredients for medicines or as intermediate compounds for preparing medicines.Type: GrantFiled: July 2, 1993Date of Patent: October 11, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuru Shiraishi, Shoji Fukumoto