Chalcogen In The Ring Patents (Class 512/11)
  • Patent number: 5831106
    Abstract: A process for preparing metallocene complexes of the general ##STR1## in which the substituents have the following meanings:M is titanium, zirconium, hafnium, vanadium, niobium or tantalum,X is fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or --OR.sup.5,where R.sup.5 is C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl, alkylaryl, aryl-alkyl, fluoroalkyl or fluoroaryl with, in each case, 1 to 10 carbon atoms in the alkyl radical and 6 to 20 carbon atoms in the aryl radical,R.sup.1 to R.sup.4 and R.sup.6 to R.sup.9 are hydrogen, C.sub.1 -C.sub.10 -alkyl, 5- to 7-membered cycloalkyl which can in turn carry C.sub.1 -C.sub.10 -alkyls as substituents, or C.sub.6 -C.sub.15 -aryl or aryl-alkyl, it also being possible where appropriate for two adjacent radicals together to be cyclic groups having 4 to 15 carbon atoms, or Si(R.sup.10).sub.3 withR.sup.10 being C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or C.sub.3 -C.sub.
    Type: Grant
    Filed: May 16, 1996
    Date of Patent: November 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Langhauser, David Fischer, Gunther Schweier, Hans-Herbert Brintzinger, Hans-Robert-Hellmuth Damrau
  • Patent number: 5831101
    Abstract: The invention concerns 14-methyl-hexadecen-11-olide, 14-methyl-hexadecen-12-olide and 14-methyl-hexadecanolide and the use of these compounds as fragrance materials with musk odour. The invention also concerns 14-methyl-12-hydroxy-hexasecanolide, which is an intermediate in a novel process to prepare these compounds.
    Type: Grant
    Filed: November 10, 1997
    Date of Patent: November 3, 1998
    Assignee: Quest International B.V.
    Inventors: David Munro, Charles Stanley Sell
  • Patent number: 5792740
    Abstract: Perfuming ingredients which include at least one macrolide of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines and wherein the symbol R represents a hydrogen atom or a methyl radical, are described. They are useful for the preparation of perfumes and perfumed consumer products to which they impart musky odors with original nuances.
    Type: Grant
    Filed: March 5, 1997
    Date of Patent: August 11, 1998
    Assignee: Firmenich SA
    Inventors: Hubert Mimoun, Pierre-Alain Blanc
  • Patent number: 5786321
    Abstract: A method for the production of .omega.-haloalkyl esters which are useful as intermediates in the synthesis of cis-oxacycloheptadec-11-en-2-one (Product I) and cis-oxacycloheptadec-12-en-2-one (Product II). Also disclosed is a process for the synthesis of Products I-II and a method for using Products I-II to impart an ambery or musky smell to a fragrance composition. Finally, fragrance compositions including Products I-II are disclosed as well as end products such as perfume extracts, toilet waters, cosmetic preparations, soaps, detergents and functional products, each of which also contains at least one of Products I-II.
    Type: Grant
    Filed: November 10, 1997
    Date of Patent: July 28, 1998
    Assignee: V. Mane Fils S.A.
    Inventors: Maurice Mane, Jean-Louis Ponge
  • Patent number: 5698514
    Abstract: Described are allyl esters of 2-norbornane acrylic acids and 2-norbornylidene propionic acids defined according to the generic structure: ##STR1## wherein the wavy line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein one of the dashed lines is carbon-carbon single bond and the other of the dashed lines is a carbon-carbon double bond; and wherein R represents methyl or hydrogen; as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: December 16, 1997
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus Johannes Wiegers, Marie R. Hanna
  • Patent number: 5665696
    Abstract: Novel odorant compositions which are characterized by a content of one or more compounds selected from the group consisting of tetrahydrofurans of structures 1 or 2, or tetrahydropyrans of structure 3. ##STR1## wherein R can be an acyclic, where acyclic refers to a chain of at least four carbon atoms substituted with at least three methyl groups in the chain, carbocyclic, where carbocyclic refers to a ring of 5-8 carbon atoms, and with at least two methyl groups on the ring, or bicyclic where bicyclic refers to two carbon tings, each ring having between 5-8 carbon atoms fused together, substituted with at least two methyl groups, and where R.sub.1 =CH.sub.3, or higher alkyl group, R.sub.2 =H, CH.sub.3, or higher alkyl group, R.sub.3 =H, or CH.sub.3, R.sub.4 and R.sub.5 =H, CH.sub.3, or higher alkyl group.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: September 9, 1997
    Assignee: Givaudan-Roure (International) SA
    Inventor: Paul David Noire
  • Patent number: 5510326
    Abstract: Novel odorant compositions which are characterized by a content of one or more compounds selected from the group consisting of tetrahydrofurans of structures 1 or 2, or tetrahydropyrans of structure 3. ##STR1## wherein R can be an acyclic, where acyclic refers to a chain of at least four carbon atoms substituted with at least three methyl groups in the chain, carbocyclic, where carbocyclic refers to a ring of 5-8 carbon atoms, and with at least two methyl groups on the ring, or bicyclic where bicyclic refers to two carbon rings, each ring having between 5-8 carbon atoms fused together, substituted with at least two methyl groups, and where R.sub.1 .dbd.CH.sub.3, or higher alkyl group, R.sub.2 .dbd.H, CH.sub.3, or higher alkyl group, R.sub.3 .dbd.H, or CH.sub.3, R.sub.4 and R.sub.5 .dbd.H, CH.sub.3, or higher alkyl group.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: April 23, 1996
    Assignee: Givaudan-Roure Corporation
    Inventor: Paul D. Noire
  • Patent number: 5482635
    Abstract: A fabric conditioning product which may be used during the rinsing or tumble drying of fabrics after washing, contains a perfume composition which contains specified ketones and salicylates. The perfumes inhibit development of human body malodour on the fabrics when worn and the combination of specified materials makes it possible to avoid inclusion of individual components with powerful, unacceptable odors.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: January 9, 1996
    Assignee: Lever Brothers Company
    Inventors: John M. Behan, Christopher F. Clements, John R. Martin, Keith D. Perring
  • Patent number: 5478803
    Abstract: Described are 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures defined according to the structure: ##STR1## wherein structure represents mixtures wherein in the mixture in each of the compounds, one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond, processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers). Also described is a process for preparing such 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures using as a starting material 2,7-octadienol having the structure: ##STR2## as well as the process intermediates having the structures: ##STR3## wherein R represents C.sub.1 -C.sub.4 alkyl; R.sub.1 and R.sub.
    Type: Grant
    Filed: October 27, 1994
    Date of Patent: December 26, 1995
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William J. Fylak, Marie R. Hanna, Futoshi Fujioka
  • Patent number: 5378685
    Abstract: Described is a process for preparing trimethyl and dimethylmethylene propyl polyhydropyran derivatives including compounds defined according to the structure: ##STR1## which defines a mixture wherein in the mixture, in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represents a carbon-carbon single bond as well as the compound having the structure: ##STR2## products produced thereby; perfumery uses of such products; process intermediates of such process including compounds defined according to the structures: ##STR3## wherein X represents chloro or bromo.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: January 3, 1995
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
  • Patent number: 5368876
    Abstract: Flavoring and perfume compositions as well as flavored foodstuffs and allied products and also perfumed products characterized by a content of one or more substituted thiophenes with the formula ##STR1## wherein none, one or two of the dotted lines represent a double bond with the proviso that no cumulated double bonds are present.
    Type: Grant
    Filed: October 28, 1992
    Date of Patent: November 29, 1994
    Assignee: Naarden-International N.V.
    Inventors: Henry L. A. Van den Heuvel, Paulus P. J. M. Jaegers
  • Patent number: 5266559
    Abstract: Perfuming composition or perfumed article containing as a perfuming ingredient at least one pentadecenolide of formula ##STR1## having a double bond of trans configuration in one of the positions 11 or 12 such as indicated by the dotted lines. Compounds (I) develop musky, animal odor notes, reminiscent of natural musk.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: November 30, 1993
    Assignee: Firmenich S.A.
    Inventors: Peter Fankhauser, Piero Fantini
  • Patent number: 5248792
    Abstract: The invention concerns odorant and flavorant compositions which contain one or more compounds of the formula ##STR1## wherein R represents an alkyl group having from three to eight carbon atoms. The invention also concerns 5-methyl-6-pentyl-tetrahydro-.alpha.-pyrone (compound of formula I in which R represents pentyl) in the form of its cis-isomer, its trans-isomer or its cis/trans isomer mixture, and a process for its manufacture by a Bayer-Villiger oxidation of 2-pentyl-3-methyl-cyclopentan-1-one. As fields of use for these compounds there come into consideration, for example, perfume and flavoring compositions, foodstuffs, semi-luxury consumables and drinks.
    Type: Grant
    Filed: May 13, 1992
    Date of Patent: September 28, 1993
    Assignee: Givaudan-Roure Corporation
    Inventor: Roman Kaiser
  • Patent number: 5219836
    Abstract: Tetrahydro-4-methyl-2-phenyl-2H-pyran is useful as a perfuming ingredient for the preparation of perfuming compositions and perfumed articles, to which it imparts odor notes of the green, rose oxide type.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: June 15, 1993
    Assignee: Firmenich SA
    Inventors: Hugh Watkins, Olamay C. Liu, James A. Krivda
  • Patent number: 5214163
    Abstract: A process for the preparation of 15-pentadecanolide, wherein bis-(13-oxabicyclo[10.4.0]hexadec-12-yl)peroxide is subjected to a thermal treatment in an organic solvent, eventually followed by hydrogenation of the resulting reaction product, which treatment is carried out in an organic solvent having a boiling point comprised between about 170.degree. and 250.degree. C.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: May 25, 1993
    Assignee: Firmenich S.A.
    Inventors: Peter Fankhauser, Piero Fantini
  • Patent number: 5196224
    Abstract: Flavoring and perfume compositions as well as flavored foodstuffs and allied products and also perfumed products characterized by a content of one or more substituted thiophenes with the formula ##STR1## wherein none, one or two of the dotted lines represent a double bond with the proviso that no cumulated double bonds are present.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: March 23, 1993
    Assignee: Naarden-International N.V.
    Inventors: Henry L. A. Van den Heuvel, Paulus P. J. M. Jaegers
  • Patent number: 5189185
    Abstract: A process for preparing furans of the formula (I) ##STR1## by reacting a furanone of the formula ##STR2## with an organic orthoacid or an orthosilicate in the presence of an acid catalyst at an elevated temperature.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: February 23, 1993
    Assignee: Henkel Corporation
    Inventors: Eugene Harris, Thomas Korte
  • Patent number: 5179077
    Abstract: The invention concerns the novel compound, 4-methyl-3-pentyl-2 (5H)-furanone, I, a process for the manufacture of I and fragrance and flavor compositions containing I.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: January 12, 1993
    Assignee: Givaudan Corporation
    Inventors: Peter M. Muller, Hans-Jakob Wild
  • Patent number: 5177057
    Abstract: Described is the reaction product of linalool with citric acid wherein the reaction is carried out at 100.degree. C. for a period of about two hours in aqueous media. The resulting reaction product contains alpha terpineol having the structure: ##STR1## The reaction product of our invention may be used to augment, enhance or impart aromas and tastes to consumable materials including perfume compositions, colognes, perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations and the like as well as foodstuffs and chewing gums.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: January 5, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael J. Zampino, Braja D. Mookherjee
  • Patent number: 5112803
    Abstract: Described is a process for the preparation of compositions of matter containing octalactones defined according to the structure: ##STR1## which includes the stereoisomers having the structures: ##STR2## by means of the sequential steps of (i) fermentation of caprylic acid or the ethyl ester of caprylic acid defined according to the generic structure: ##STR3## wherein R is hydrogen or ethyl using a microorganism selected from the group consisting of:Mortierella isabellina, ATCC 44583;Mortierella isabellina, ATCC 38063;Syncephalastrum racemosum, NRRL A-5889;Mortierella isabellina, IFO 7884;Mortierella ramanniana var. angulispora, IFO 8187;Mortierella isabellina, CBS 221.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: May 12, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, Lynda B. McLean, James A. Morris, Henry A. Bondarovich
  • Patent number: 5021402
    Abstract: Cyclic ethers of formula ##STR1## wherein the dotted line indicates the location of a single or double bond and the symbol R represents an isopropenyl radical or a 1-ethoxy-1-methylethyl radical, are novel compounds with useful organoleptic properties. They can be used as active ingredients in perfuming compositions and perfumed products to which they confer rosy-fruity type odor notes. In addition, they possess flavor qualities which render these compounds useful for flavoring foodstuffs and drinks and, namely, mango-type drinks.A process for the preparation of the compounds of formula (I) is also disclosed.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: June 4, 1991
    Assignee: Firmenich SA
    Inventors: Anthony F. Morris, Regula Naef, Sina Escher, Alain Velluz
  • Patent number: 4980342
    Abstract: A convenient process for the preparation of .gamma.-alkyl-substituted-.gamma.-butyrolactones and .delta.-valerolactones is provided. The process involves forming the .alpha.-alkylidene lactone by reacting essentially equimolar amounts of an .alpha.-acyl lactone, an aldehyde, and an alkali metal hydroxide in an inert diluent at an elevated temperature while removing water and hydrogenating the .alpha.-alkylidene lactone to obtain the corresponding .alpha.-alkyl lactone.
    Type: Grant
    Filed: September 1, 1989
    Date of Patent: December 25, 1990
    Assignee: Henkel Corporation
    Inventors: Louis Rebrovic, Eugene G. Harris
  • Patent number: 4963285
    Abstract: Described are 2,4,4-trisubstituted tetrahydro pyranyl esters defined according to the structure: ##STR1## wherein R.sub.1 represents methyl or ethyl and R.sub.2 represents C.sub.2 -C.sub.4 straight chain or branched chain alkyl or alkenyl and organoleptic used thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including, but not limited to bleach compositions, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: October 16, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Roger E. Greene
  • Patent number: 4962090
    Abstract: Described are 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers defined according to the generic structure: ##STR1## wherein R' represents methyl or ethyl; R.sub.1 and R.sub.2 taken alone are the same or different hydrogen, phenyl, C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) and R.sub.1 and R.sub.2 taken together represent C.sub.5 -C.sub.12 cycloalkyl or alkyl cycloalkyl, and reaction products containing said 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers taken alone or taken further together in admixture with compounds defined according to the generic structure: ##STR2## wherein in the compounds defined according to the structure: ##STR3## one of the dashed lines in the moiety: ##STR4## represents a carbon-carbon double bond and each of the other dashed lines represent carbon-carbon single bonds; and R.sub.1 ' and R.sub.2 ' taken alone or taken together are defined in the same manner that R.
    Type: Grant
    Filed: March 22, 1990
    Date of Patent: October 9, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Salvatore M. Brucato, Charles E. J. Beck, Marie R. Hanna
  • Patent number: 4937229
    Abstract: A compound of the general formula, ##STR1## wherein R.sub.1 and R.sub.2 independently are --H, --CH.sub.3, or --CH.sub.2 CH.sub.3 ; and R.sub.3 is alkyl of from 1 to 10 carbons or aryl of from 6 to 10 carbons.
    Type: Grant
    Filed: June 26, 1989
    Date of Patent: June 26, 1990
    Assignee: Hercules Incorporated
    Inventors: Brian Byrne, Louise M. L. Lawter
  • Patent number: 4914083
    Abstract: Described are oxy-substituted-2-phenyl pyran derivatives defined according to the generic structure: ##STR1## wherein: (i) the dashed lines in the pyran ring each represents a carbon-carbon single bond; or one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines in the pyran ring is a carbon-carbon single bond;(ii) wherein R.sub.2 represents lower alkyl and R.sub.1 is hydrogen; or(iii) R.sub.1 and R.sub.2 represented by the moiety: ##STR2## taken together represents methylene and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations and cosmetic powders.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: April 3, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus J. Wiegers, Anton Van Ouwerkerk
  • Patent number: 4906610
    Abstract: Described is the tetrahydro-5-isopropyl-2-methyl-2-thiophene acetonitrile of our invention having the structure: ##STR1## and organoleptic uses thereof in augmenting or enhancing the aroma or taste of perfume compositions, colognes, perfumed articles, foodstuffs and chewing gums.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 6, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Joseph A. McGhie
  • Patent number: 4877769
    Abstract: Described are the 6,7-(epithio)-3,7-dimethyl-1,3-octadienes having the structures ##STR1## and mixtures of same as well as the uses thereof in augmenting or enhancing the aroma or perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic powders, hair preparations and the like.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: October 31, 1989
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael J. Zampino, Richard A. Wilson, Braja D. Mookherjee, Jean C. Niel
  • Patent number: 4742044
    Abstract: Described are the aralkoxy, alkoxy, alkadienyloxy and alkenyloxy-1,3,2-dioxaborinane derivatives defined according to the genus: ##STR1## (wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different hydrogen, methyl and ethyl; and wherein R represents C.sub.6 straight chain alkenyloxy; C.sub.10 branched chain alkenyloxy; C.sub.12 aralkoxy; C.sub.12 branched chain alkoxy; or C.sub.10 branched chain alkadienyloxy) and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, particularly drier-added fabric softener articles and perfumed polymers.
    Type: Grant
    Filed: August 19, 1987
    Date of Patent: May 3, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Richard M. Boden
  • Patent number: 4731356
    Abstract: 2,3-Epoxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone, an epoxy ketone of formula ##STR1## possess useful fragrance characters and, consequently, it can be used advantageously in the manufacture of perfume, perfume bases and perfumed products. It develops a flowery and fruity odor.
    Type: Grant
    Filed: June 4, 1987
    Date of Patent: March 15, 1988
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Dietrich Kastner
  • Patent number: 4717506
    Abstract: The present invention relates to a novel pyran derivative mixture represented by the following general formula (I): ##STR1## wherein R.sub.1 is H or CH.sub.3, R.sub.2 is CH.sub.2 or CH.sub.3, one of the bonds X, Y, or Z is a double bond and the remaining two bonds are single bonds. The present invention relates to a process for the preparation of the above-mentioned pyran derivative mixture. The pyran derivative compound (I) of the present invention is produced by reacting a compound represented by the following formula (II): ##STR2## with a compound represented by the general formula (III): ##STR3## in the presence of an acid catalyst wherein R.sub.1 is as defined above. In addition, the present invention relates to a perfume composition containing an effective aromal amount of the pyran derivative compound represented by the general formula (I) above, in the presence of an acceptable carrier therefore.
    Type: Grant
    Filed: January 22, 1986
    Date of Patent: January 5, 1988
    Assignee: Kao Corporation
    Inventors: Hiroshi Takada, Shin'ichi Masuda, Motoki Nakajima
  • Patent number: 4707302
    Abstract: 2-Substituted 4,4,7,7-tetramethyl-1,3-dioxacycloheptanes of the general formula I ##STR1## where R.sup.1 is a straight-chain or branched alkyl of 1 to 10 carbon atoms which additionally may contain oxygen in the form of an ether group or is 5- to 8-membered cycloalkyl of up to 10 carbon atoms which may additionally contain oxygen in the form of an ether group, of which particularly interesting representatives are 2,4,4,7,7-pentamethyl-1,3-dioxacycloheptane, 2-tert.-butyl-4,4,7,7-tetramethyl-1,3-dioxacycloheptane and 2-isopropyl-4,4,7,7-tetramethyl-1,3-dioxacycloheptane, are prepared and used as scents.
    Type: Grant
    Filed: February 3, 1987
    Date of Patent: November 17, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Hardo Siegel