Patents Examined by Bernard Helfin
  • Patent number: 4528402
    Abstract: Described are hydrocarbyloxy alkanals defined according to the generic structure: ##STR1## wherein R.sub.1 represents one of the moieties: ##STR2## and R.sub.2 represents hydrogen or methyl prepared according to the process of first reacting an allyl alcohol defined according to the structure: ##STR3## with a hydrocarbon or hydrocarbyl halide defined according to the structure:R.sub.1 '--Xhaving an electrophilic center wherein R.sub.1 ' is saturated or unsaturated hydrocarbyl and X represents halogen or hydrogen with the provisos that:R.sub.1 ' is saturated hydrocarbyl when X is halogen andR.sub.1 ' is unsaturated hydrocarbyl when X is hydrogen.Also described are organoleptic uses of such hydrocarbyloxy alkanals in the field of perfumery, colognes and perfumed articles, (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: July 9, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William L. Schreiber, Futoshi Fujioka, Patrick Chant, Lambert Dekker
  • Patent number: 4528406
    Abstract: Production of bis(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of a particular acidic clay catalyst, quenching of the catalyst and recovery of the desired ether by distillation directly from the reaction mixture containing the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distilland product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.
    Type: Grant
    Filed: November 30, 1983
    Date of Patent: July 9, 1985
    Assignee: Atlantic Richfield Company
    Inventors: Mary T. Arnold, George R. Siciliano
  • Patent number: 4528391
    Abstract: The reaction between a hydroxyl-containing material and an isocyanate-containing material is catalyzed by a pyrazino pyrazine compound such as 1,4,5,8-tetramethyldecahydropyrazino(2,3-b)pyrazine.
    Type: Grant
    Filed: November 28, 1983
    Date of Patent: July 9, 1985
    Assignee: The Dow Chemical Company
    Inventors: Duane S. Treybig, James L. Potter
  • Patent number: 4524017
    Abstract: Norbornane derivatives having hydrocarbon side chains, the processes for preparing the same and perfume compositions containing the same. The norbornane derivatives are represented by the following general formula (I) ##STR1## wherein C.sub.2 is an ethyl group, an ethylidene group or a vinyl group each connected to 5 or 6 position of the norbornane ring, each of R.sub.1 and R.sub.2 is a hydrogen atom or a methyl group, and R.sub.3 is a formyl group or a group represented by the following general formula (II) ##STR2## wherein R.sub.4 is a methyl group, an ethyl group, a n-propyl group or an isopropyl group, and X is a carbon atom of the norbornane ring. The above norbornane derivatives give a wide variety of woody fragrances and are useful as components for various perfume products.
    Type: Grant
    Filed: February 24, 1982
    Date of Patent: June 18, 1985
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Yoshiharu Inoue, Fumio Tanimoto, Hisao Kitano
  • Patent number: 4523025
    Abstract: A polymer polyol made by the reaction of a partially reacted polyamine with an organic polyisocyanate in a polyether polyol solvent of about 3,000 to 8,000 molecular weight is disclosed. Preferably, the polyisocyanate is reacted with a partially alkoxylated polyoxyalkylenediamine. This polymer polyol may be used in the manufacture of flexible polyurethane foams with improved properties. The polymer polyols are more stable than those made by other procedures.
    Type: Grant
    Filed: October 21, 1983
    Date of Patent: June 11, 1985
    Assignee: Texaco Inc.
    Inventors: Michael Cuscurida, Howard P. Klein
  • Patent number: 4522748
    Abstract: Bicyclic aldehydes of formula ##STR1## possess useful organoleptic properties and can be used advantageously as perfume and flavor ingredients. Compounds (I) develop woody and ambery odor notes and woody, musky and earthy gustative characteristics. They are prepared by a multistep process starting from (E)-13-norcaryophyll-4-en-8-one.
    Type: Grant
    Filed: August 19, 1983
    Date of Patent: June 11, 1985
    Assignee: Firmenich SA
    Inventors: Bruno Maurer, Arnold Hauser
  • Patent number: 4521637
    Abstract: Production of bis-(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of an aryl sulfonic acid treated calcined alumina catalyst, quenching the catalyst with a basic compound and recovery of the desired ether by distillation following separation of the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distilled product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.
    Type: Grant
    Filed: December 16, 1983
    Date of Patent: June 4, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Frank Stevens
  • Patent number: 4521630
    Abstract: Aldehydes are prepared by hydrogenating a compound of general formula R'COOR, wherein R represents a hydrogen atom, an alkyl or an acyl group, or a metal, and R' represents an optionally substituted hydrocarbyl group having at most two alpha-hydrogen atoms, provided it has at most one beta-hydrogen atom, in case it has two alpha-hydrogen atoms, in the presence of a catalyst comprising at least one metal selected from rare earth metals and iron on an alumina-based carrier.
    Type: Grant
    Filed: August 9, 1983
    Date of Patent: June 4, 1985
    Assignee: Shell Oil Company
    Inventors: Freddy Wattimena, Hendricus J. Heijmen
  • Patent number: 4521636
    Abstract: Preparation of bis-(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of an aluminum sulfate treated calcined alumina catalyst, quenching of the catalyst and recovery of the desired ether by distillation following separation of the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distill and product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.
    Type: Grant
    Filed: December 16, 1983
    Date of Patent: June 4, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Wayne A. Kriel
  • Patent number: 4521633
    Abstract: Prepare high purity perbrominated aromatic compounds, especially decabromodiphenyl oxide, by adding an aromatic compound to a mixture comprising an organic solvent, a catalyst, and a slight stoichiometric excess of bromine, at a low initial reaction temperature.
    Type: Grant
    Filed: May 19, 1983
    Date of Patent: June 4, 1985
    Assignee: The Dow Chemical Company
    Inventor: Joseph J. Pedjac
  • Patent number: 4521634
    Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: June 4, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4518808
    Abstract: Disclosed is a process for the preparation of certain dichloro-hydroxy and alkoxy aromatic compounds by reacting the corresponding unchlorinated compound with sulfuryl chloride in the presence of acetic acid, propionic acid or lower alkyl esters thereof.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: May 21, 1985
    Assignee: Eastman Kodak Company
    Inventors: Richard H. S. Wang, Garry L. Myers
  • Patent number: 4518805
    Abstract: Described herein is a process for the conversion of hydroperoxides, present in allyl-alkyl ethers to products including .alpha.,.beta.-unsaturated aldehydes and for reducing such .alpha.,.beta.-unsaturated aldehydes to alcohols prior to the use of the ether as a feedstock in a hydroformylation reaction to produce the corresponding ether aldehyde. The process involves contacting the ether with a metal hydride, either in aqueous solution and/or by means of an ion exchange resin. Such treatment decomposes the hydroperoxides and then reduces their .alpha.,.beta.-unsaturated aldehyde decomposition products, thereby reducing the catalyst inhibition period present in the hydroformylation reaction which is observed when such .alpha.,.beta.-unsaturated aldehyde impurities are present.
    Type: Grant
    Filed: February 14, 1983
    Date of Patent: May 21, 1985
    Assignee: Union Carbide Corporation
    Inventors: Anthony G. Abatjoglou, David R. Bryant
  • Patent number: 4518806
    Abstract: The synthesis of aryl alkyl ethers from methylbenzyl alcohol and, optionally, phenol using a bis-(dithiobenzyl)nickel(II) catalyst is disclosed.
    Type: Grant
    Filed: July 1, 1983
    Date of Patent: May 21, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Haven S. Kesling, Jr.
  • Patent number: 4515987
    Abstract: Described is a genus of compounds defined according to the structure: ##STR1## (Z) represents one of the moieties ##STR2## as well as the substantially pure compound defined according to the structure: ##STR3## and the use thereof for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, perfumed articles, hair preparations and the like.
    Type: Grant
    Filed: June 26, 1984
    Date of Patent: May 7, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Theodore J. Tyszkiewicz, Michael Licciardello, Manfred H. Vock, Joaquin F. Vinals, Patrick Whalen, Marie R. Hanna
  • Patent number: 4515988
    Abstract: Compounds of the formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group, or a cyano group,Y is a hydrogen atom, a halogen atom, or a trihalomethyl group, andZ is a hydroxy group, an alkoxy group, an alkyl group, a halogen atom, an amino group, an alkylthio group, a cyano group, a carboxy group, a carbalkoxy group, a carboxyalkyl group, a carbalkoxyalkyl group, an alkanoyloxy group, or a carbamoyloxy group,and compositions containing these compounds exhibit herbicidal activity.
    Type: Grant
    Filed: September 16, 1981
    Date of Patent: May 7, 1985
    Assignee: Rohm and Haas Company
    Inventors: Horst O. Bayer, Colin Swithenbank, Roy Y. Yih
  • Patent number: 4514576
    Abstract: The synthesis of aryl alkyl ethers from methylbenzyl alcohol and, optionally, phenol using a rhenium heptoxide catalyst is disclosed.
    Type: Grant
    Filed: July 1, 1983
    Date of Patent: April 30, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Haven S. Kesling, Jr.
  • Patent number: 4511730
    Abstract: This invention relates to carbamates of beta-hydroxyethylsulfoxides which are useful as cosurfactants in enhanced oil recovery, surfactants and biocides, and as hydraulic fluids when of sufficiently low molecular weight.
    Type: Grant
    Filed: August 17, 1982
    Date of Patent: April 16, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventor: Ellis K. Fields
  • Patent number: 4511731
    Abstract: Preparation of monoethers of dihydroxybenzenes from an isopropenylphenol and an alkylating agent and thereafter oxidizing in the presence of an acid catalyst.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: April 16, 1985
    Assignee: The Dow Chemical Company
    Inventors: Abel Mendoza, Eric W. Otterbacher
  • Patent number: 4510334
    Abstract: In a method for the removal of alkali halides by washing them out of reaction products prepared, in the presence of ketones which form a miscibility gap with water, by a reaction of xylylene dichlorides and/or bromides with bisphenols in the presence of alkaline compounds or in the form of alkali salts, at 85.degree. to 160.degree. C., with the addition in some cases of terminal-group-closing monophenols or monohalogen alkyl compounds, water or a water-ketone mixture solvent is added to the reaction mixture before beginning the filtration, and afterward is recycled. For the complete recovery of the ketones and alkali halides and the reuse of the ketones with reduced energy consumption a kentonous phase and an aqueous phase are recovered by separate evaporation after the separation of the filtrate in two liquid phases, both of the condensates are combined to a ketone-water mixture, the filter cake is stirred up again in the ketone-water mixture and filtered a second time.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: April 9, 1985
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Dirk Glembin, Kurt Huhn, Gunter Meyer, Manfred Thallmeier