Benzene Ring Patents (Class 512/20)
  • Patent number: 5562847
    Abstract: The present invention relates to dryer-activated fabric softening compositions comprising: (A) fabric softening compounds; and (B) an ester of an alcohol perfume wherein the ester has at least one free carboxylic acid. The ester has the general formula: ##STR1## wherein R is selected from the group consisting of substituted or unsubstituted C.sub.1-C.sub.30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, aryl group; or ring containing a heteroatom, R' is a perfume alcohol with a boiling point at 760 mm Hg of less than about 300 .degree. C.; and m and n are independently an integer of 1 or greater.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: October 8, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Scott W. Waite, John C. Severns, Mark R. Sivik, Frederick A. Hartman
  • Patent number: 5552380
    Abstract: Described are phenyl alkanol derivatives defined according to the structure: ##STR1## wherein R.sub.1 is methyl or ethyl and R.sub.2 is hydrogen or acetyl with the proviso that when R.sub.2 is hydrogen, R.sub.1 is ethyl and when R.sub.2 is acetyl, R.sub.1 is methyl and uses thereof in augmenting, enhancing or imparting an aroma in or to perfume compositions, colognes and perfumed articles including but not limited to solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: September 3, 1996
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna
  • Patent number: 5527768
    Abstract: Described is the use of 1-benzyl cyclohexanol having the structure: ##STR1## in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles such as perfumed polymers and solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles. Also described are processes and compositions for use of the 1-benzyl cyclohexanol of our invention having the structure: ##STR2## in perfume aroma augmenting, enhancing, modifying and altering compositions and as perfume, cologne and perfumed article aroma imparting compositions. Such compositions may also have imparted thereto as a result of using 1-benzyl cyclohexanol having the structure: ##STR3## insect repellency.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: June 18, 1996
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Charles E. J. Beck
  • Patent number: 5527769
    Abstract: The compounds of formula ##STR1## wherein symbol X represents a --CHO group or an acetal group of formula ##STR2## symbols R', taken separately, represent each a C.sub.1 to C.sub.4, linear or branched, saturated or unsaturated, hydrocarbon radical or, taken together, represent a C.sub.1 to C.sub.4 alkylene radical, which may be substituted, and symbol R represents a hydrogen atom or a methyl radical, are useful as perfuming ingredients for the preparation of perfuming compositions and perfumed articles, to which they impart floral type notes.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: June 18, 1996
    Assignee: Firmenich SA
    Inventors: Beat Winter, George Skouroumounis
  • Patent number: 5501805
    Abstract: Compositions of fragrance materials having an Odour Intensity Index of less than 110, and a Malodour Reduction Value of at least 0.25 or an Odour Reduction Value of at least 0.25, can be used as fragrance compositions in detergent powders, detergent liquids, soap or detergent bars or pastes, fabric-conditioning compositions in liquid or solid form, or personal body deodorant compositions, to confer deodorant effects in use even though they have in themselves a low or imperceptible level of fragrance (Odour Intensity Index).
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: March 26, 1996
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: John M. Behan, Christopher F. Clements
  • 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: 5462923
    Abstract: Described are 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives, wherein the 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes are defined according to the structure: ##STR1## wherein Y.sub.1 represents one of the moieties: ##STR2## and wherein the bicyclopentadiene derivatives are defined according to the structure: ##STR3## wherein Z.sub.1 and Z.sub.2 represent hydrogen, C.sub.1 -C.sub.3 lower alkyl or C.sub.2 -C.sub.3 acyl and Z.sub.3 represents methyl or hydrogen with the proviso that Z.sub.1 and Z.sub.2 are not both hydrogen, and uses thereof in augmenting, enhancing or imparting aromas in and to perfume compositions, colognes, perfumed polymers and perfumed articles.
    Type: Grant
    Filed: September 2, 1994
    Date of Patent: October 31, 1995
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Richard A. Weiss, Mark D. Evans, Marie R. Hanna
  • Patent number: 5372995
    Abstract: Described is a two-step process for producing phenyl- and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention by means of first reacting methyl ethyl ketone with benzaldehyde in the presence of a sulfonic acid catalyst to produce a mixture of phenyl pentenone derivatives; and then hydrogenating the resulting mixture of phenyl pentenone derivatives in the presence of a hydrogenation catalyst, as well as the product produced thereby; and perfumery uses thereof for augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: December 13, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna
  • Patent number: 5281576
    Abstract: Described are aryl oxabicyclooctane derivatives and phenyl norbornane derivatives defined according to the structures: ##STR1## wherein N is an integer selected from the group consisting of 1 and 2, processes for preparing same, perfumery uses thereof and intermediates used in said processes which intermediates are defined according to the structures: ##STR2## wherein M is 0, 1 or 2 and X is chloro or bromo. Also described are the by-products having the structure: ##STR3## wherein P is 1 or 2 and uses thereof in perfumery.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: January 25, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio
  • Patent number: 5248831
    Abstract: Ethers of 1-hydroxy-hex-5-en-2-one are useful odoriferous substances which have a very complex fragrance pattern and allow an interesting variation in the scent of perfume oils.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: September 28, 1993
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
  • Patent number: 5221780
    Abstract: A 1-(2,6-dimethylphenyloxy)-2-alkanol of formula (1): ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms, and perfume compositions containing the alkanol having an intense woody note, and are useful as fragrance-imparting ingredients for various compositions, particularly in the cosmetic field.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: June 22, 1993
    Assignee: Kao Corporation
    Inventors: Junji Koshino, Nao Toi, Katsuhiko Tajima, Yoshiaki Fujikura
  • Patent number: 5196613
    Abstract: The invention concerns a novel process for the manufacture of 2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene, 1, commonly known as .alpha.-ambrinol. ##STR1## The process comprises reducing either an 8-halo-2-hydroxy-2,5,5-trimethyl-2,3,4,4a,5,6,7,8-ociahydronaphihalene (11a), alone or in admixture with a 1-halo-2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (11b), or reducing the 1,2-epoxide which can be formed therefrom, namely, 1,2-epoxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphihalene (111). The halohydrins 11 are prepared from 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydronaphihalene, IV.The compounds of formulas II and III are novel and form part of the present invention. The formula III epoxide possesses valuable odorant properties and its use as an odorant also forms part of the invention.
    Type: Grant
    Filed: January 21, 1991
    Date of Patent: March 23, 1993
    Assignee: Givaudan Corporation
    Inventor: Peter Naegeli
  • Patent number: 5086038
    Abstract: Aromatic aldehydes of formula ##STR1## possessing a single or a double bond in the position indicated by the dotted line and wherein symbol X represents a monovalent radical or formula ##STR2## or, when the dotted line represents a single bond, of formula ##STR3## and wherein symbol Z stands for an oxygen atom or for two R.sup.2 O radicals, each of R.sup.1 and R.sup.2 representing an alkyl radical having from 1 to 3 carbon atoms.Aromatic aldehydes (I) possess useful odorous properties and can be used as perfuming ingredients for the preparation of perfume bases and perfumed articles. They can also be used as starting materials for the preparation of useful end-products having herbicide and fungicide properties.Process for the preparation of aromatic aldehydes (I) starting from 8-methoxycuminic aldehyde.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: February 4, 1992
    Assignee: Firmenich SA
    Inventors: Ferdinand Naef, Francois Delay, Arnoldus Uijttewaal
  • Patent number: 4990494
    Abstract: Described are 1,1-dimethyl-1-nitrilo or hydroxylamino-3-(alkyl phenyl)-substituted propanes defined according to the generic structure: ##STR1## wherein R.sub.1 is selected from the group consisting of: (i) cyanide having the structure: ##STR2## (ii) hydroxylamino methyl having the structure: ##STR3## and wherein R.sub.2 is C.sub.1 -C.sub.5 lower alkyl, uses 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. Also described are processes for preparing such 1,1-dimethyl-1-nitrilo or hydroxylamino-3-(alkyl phenyl)-substituted propanes by means of reacting an alkyl benzyl halide with isopropyl cyanide in the presence of a basic catalyst such as sodamide.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: February 5, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Eleanor Fox
  • Patent number: 4985402
    Abstract: Described are 2-methyl-1-nitrilo- or 2-methyl-1-hydroxylamino-3-(methoxyphenyl) propanes defined according to the generic structure: ##STR1## wherein R.sub.1 is selected from the group consisting of: (i) cyanide having the structure: ##STR2## (ii) hydroxylaminomethyl having the structure: uses 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. Also described are processes for preparing such 2-methyl-1-nitrillo- or 2-methyl-1-hydroxylamino-3-(methoxyphenyl) propanes by means of reacting a methoxy benzyl halide with ethyl cyanide in the presence of a basic catalyst such as sodamide.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: January 15, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, De Virgilio John J.
  • Patent number: 4968668
    Abstract: 2-Methyl-3-(3-methylphenyl)-propan-1-ol, 2-methyl-3-(3,5-dimethylphenyl)-propan-1-ol, 1-(3-methylphenyl)-2-methylbutan-3-ol and 1-(3,5-dimethylphenyl)-2-methylbutan-3-ol, their preparation and use as fragrances.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: November 6, 1990
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Walter Hafner, Walter Gebauer, Marlies Regiert, Wilhelm Friedrich, Erich Markl
  • Patent number: 4937073
    Abstract: A reformed vetiverol comprising 40% by weight or more of khusimol and 10% by weight or less of isovalencenol is disclosed. The vetiverol, containing a small amount of isovalencenol and a large amount of khusimol imparts a milder and more elegant odor than conventional vetiver oils or vetiverols. The reformed vetiverol can be prepared by a process comprising: esterifying alcohol components in a vetiver oil or a vetiverol, heating the esterified vetiver oil or a vetiverol to thermally decompose isovalencenol esters, hydrolyzing the remaining esters into alcohols, and separating the formed alcohols.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: June 26, 1990
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Junji Koshino, Hiroaki Uchida, Manabu Fujita, Nao Toi
  • 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: 4879271
    Abstract: Described are the schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R" represents ethyl or methyl with ketones and aldehydes defined according to the structure: ##STR2## wherein R' represents methyl or hydrogen and R represents one of the moieties: ##STR3## including compounds defined according to the generic structure: ##STR4## wherein R, R' and R" are defined, supra. Also described are uses of such schiff base reaction products in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, perfumed articles (including perfumed polymers, detergents and fabric softeners), colognes, foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos. The schiff base reaction products of our invention also have unexpected, unobvious and advantageous utilities for their deodorancy properties in addition to having valuable properties as fragrance materials and as flavor materials.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: November 7, 1989
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja D. Mookherjee, Robert W. Trenkle, Nicholas Calderone, Keith P. Sands
  • Patent number: 4853369
    Abstract: Described is the schiff base reaction product of methyl anthranilate having the structure: ##STR1## with ethyl vanillin having the structure: ##STR2## a compound having the structure: ##STR3## and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles including perfumed polymers and colognes. The schiff base having the structure: ##STR4## also has unexpected, unobvious and advantageous utilities for its deodorancy properties in addition to having valuable properties as a fragrance material.
    Type: Grant
    Filed: June 3, 1988
    Date of Patent: August 1, 1989
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja D. Mookherjee, Robert W. Trenkle, Nicholas Calderone, Ronald S. Fenn
  • Patent number: 4839083
    Abstract: Described are schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R.sub.3 represents methyl or ethyl; helional having the structure: ##STR2## and aldehydes having the generic structure: ##STR3## wherein R represents a hydrocarbyl or hydroxy hydrocarbyl moiety including the aldehydes:(a) pinoacetaldehyde having the structure: ##STR4## (b) pinoisobutyraldehyde having the structure: ##STR5## and (c) lyral, a mixture of compounds having the structures: ##STR6## and derivatives there and organoleptic uses thereof in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums and beverages.
    Type: Grant
    Filed: March 4, 1988
    Date of Patent: June 13, 1989
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja D. Mookherjee, Robert W. Trenkle, Nicholas Calderone, Lisa Schreck, Keith P. Sands
  • Patent number: 4791098
    Abstract: 2-methyl-3-(p-methylphenyl)-propionitrile is prepared for use as a scent.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: December 13, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Roland Martin, Walter Gramlich
  • Patent number: 4788177
    Abstract: It was found that ekylic ethers of 2,2,2-trichloro-1-phenylethanol with the general formula A ##STR1## are excellently usable as odoriferous substances, especially as components of perfume oils for cosmetic and technical consumer goods.
    Type: Grant
    Filed: July 27, 1987
    Date of Patent: November 29, 1988
    Inventors: Ernst-Joachim Brunke, Claus-Hermann Kappey
  • Patent number: 4756840
    Abstract: Described is the novel compound genus, the beta-alkylidene phenethyl alcohols of our invention, defined according to the generic structure: ##STR1## (wherein R.sub.1 represents hydrogen or methyl, useful in augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener articles, fabric softener compositions, cosmetic powders and hair preparations).
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: July 12, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko
  • Patent number: 4755503
    Abstract: Fragrance compositions prepared by adding thereto an olfactorily effective amount of substantially pure 2,4,6-tribromo-3-methylanisole are disclosed.
    Type: Grant
    Filed: October 21, 1987
    Date of Patent: July 5, 1988
    Assignee: Givaudan Corporation
    Inventors: Joachim E. Freudewald, Kenneth L. Purzycki, Joseph A. Virgilio
  • Patent number: 4749682
    Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances having a long-lasting flowery and somewhat spicy odor with a not very pronounced sulphurous note and corresponding to the formula ##STR1## wherein R represents a methyl or ethyl group.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: June 7, 1988
    Assignee: Naarden International N.V.
    Inventors: Pieter J. De Valois, Theo Heideman, Hans J. Wille, Henry L. A. Van Den Heuvel
  • Patent number: 4738951
    Abstract: A perfume composition is disclosed, containing methyl l-3,7-dimethyl-7-hydroxyoctylideneanthranilate of the following formula (I): ##STR1## The perfume composition of the invention is less allergenic and safer than those containing the corresponding d- or dl-form. Further, the perfume composition has a less irritating odor and imparts a clean and green note.
    Type: Grant
    Filed: June 25, 1987
    Date of Patent: April 19, 1988
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Takeshi Yamamoto, Kazutoshi Sakurai, Susumu Watanabe, Atsushi Kinosaki
  • Patent number: 4727058
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in aqueous media and in the presence of a food grade or natural nonionic emulsifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: February 23, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
  • Patent number: 4710316
    Abstract: Compounds of the general formula (I) ##STR1## and compounds of the general formula (II) ##STR2## in which R.sup.1 represents --OH, --CH.sub.2 OH, --CH.sub.2 --OCH.sub.3, --CHOH--CH.sub.3, --CHO or --CH(OCH.sub.3).sub.2,R.sup.2 represents methyl or ethyl,R.sup.3 represents hydrogen or methyl, andX represents hydrogen or methyl, are disclosed.Processes for the manufacture of certain compounds of formula (I) and for those of formula (II) are also provided. The compounds are useful as perfume materials.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: December 1, 1987
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Walter Hafner, Peter Ritter, Helmut Gebauer, Marlies Regiert
  • Patent number: 4689175
    Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances which have a very natural leather odor and correspond to the formula ##STR1## wherein one of the two symbols R.sub.1 and R.sub.2 represents a methyl group and the other a hydrogen atom or both symbols represent a hydrogen atom and R.sub.3 represents a n-propyl, allyl, 1-propenyl-, sec.butyl, 1-buten-3-yl, isobutyl or 2-methylpropen-3-yl group.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: August 25, 1987
    Assignee: Naarden International N.V.
    Inventor: Nicolaas L. J. M. Broekhof