Six-membered Alicyclic Ring Patents (Class 512/22)
  • Patent number: 6632788
    Abstract: The compound according to the formula set forth below where A is B is or A and B together form the ring structure and X, R′ and R are independently H and CH3 and m=0 or 1. and the use of the compound in creating fragrances, and scents in items such as perfumes, colognes and personal care products is disclosed.
    Type: Grant
    Filed: May 17, 2001
    Date of Patent: October 14, 2003
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anthony T. Levorse, Jr., Anubhav P.S. Narula, Edward Mark Arruda, Charles E.J. Beck
  • Publication number: 20030148919
    Abstract: Compounds of the formula (I): 1
    Type: Application
    Filed: November 21, 2002
    Publication date: August 7, 2003
    Inventors: Thomas Markert, Ralph Nemitz, Theo Ten Pierik
  • Patent number: 6551987
    Abstract: The present invention relates to fragrance delivery systems which comprise: a) one or more pro-fragrances having formula (I) wherein G1 and G2 are methyl, or a cyclic hydrocarbyl unit derived from the isomers of ionone and/or damascone; R and R1 are each independently C1-C22 substituted or unsubstituted, branched or unbranched alkyl, C2-C22 substituted or unsubstituted, branched or unbranched alkenyl, C2-C20 substituted or unsubstituted, branched or unbranched hydroxyalkyl, C7-C20 substituted or unsubstituted alkylenearyl, C3-C20 substituted or unsubstituted cycloalkyl, alkyleneoxy, C6-C20 aryl, C5-C20 heteroaryl comprising one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof; two of the units Y1, Y2, R or R1 can be taken together to form one or more aromatic or non-aromatic, heterocyclic or non-heterocyclic, single rings, fused rings, bicyclo rings, spiroannulated rings, or mixtures thereof, said rings comprising from 3 to 20 carbon atoms and one or mor
    Type: Grant
    Filed: October 22, 2001
    Date of Patent: April 22, 2003
    Assignee: The Procter & Gamble Company
    Inventors: Gregory Scott Miracle, Lon Montgomery Gray
  • Patent number: 6495512
    Abstract: Described are synergistic antimicrobial-fragrance compositions including broad spectrum antimicrobial compositions containing salicylaldehyde and at least one organoleptically-compatible antimicrobial synergism cofactor substance. The weight ratio range of salicylaldehyde:synergism cofactors substance is from 1:10 up to 10:1. The cofactor substance is such that the degree of synergism of the resultant mixture is defined according to the IFF Antimicrobial Synergism Test wherein the difference between the actual and expected antimicrobial values of the mixture is greater than or equal to a multiple of (i) 0.05 and (ii) the expected antimicrobial value of the mixture. Cofactor substances include phenolics such as cresol, caravacrol and thymol; ethyl vanillin; benzyl alcohol; indol; &bgr;-orcinol; and terpinenol-4.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: December 17, 2002
    Assignees: International Flavors & Fragrances Inc., South Bank University Enterprises Ltd., Cosar Ltd.
    Inventors: Michael John Robert White, Maria Therese Lis-Balchin, Elisabeth J. M. Simpson, Stanley G. Deans, Remco Johannes Hendrik De Meijere
  • Patent number: 6489273
    Abstract: A fragrance, having a 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by formula (1), wherein R represents a hydrogen atom or an acetyl group, Me represents a methyl group and n represents an integer from 0 to 3, provides a very pleasing scent, has excellent stability in a product, and can be mixed well with other fragrances.
    Type: Grant
    Filed: November 28, 2000
    Date of Patent: December 3, 2002
    Assignee: Takasago International Corporation
    Inventors: Takashi Aida, Hiroyuki Matsuda, Tetsuro Yamasaki
  • Publication number: 20020173444
    Abstract: The present invention is directed to the use of an olfactory acceptable amount comprising tetrahydro-4-methylene-2-(4-methoxyphenyl)-2H-pyran, 5,6-dihydro-4-methyl-2-(4-methoxyphenyl)-2H-pyran, 3,6-dihydro-4-methyl-2-(4-methoxyphenyl)-2H-pyran and mixtures of these materials which are useful in creating fragrances, and scents in items such as perfumes, colognes and personal care products.
    Type: Application
    Filed: March 12, 2001
    Publication date: November 21, 2002
    Inventors: Mark A. Sprecker, Charles E.J. Beck
  • Publication number: 20020137660
    Abstract: The present invention relates to a process for the preparation of alkylcarboxylic allyl esters by reacting allyl alcohol and alkylcarboxylic acids.
    Type: Application
    Filed: March 18, 2002
    Publication date: September 26, 2002
    Inventors: Walter Kuhn, Gerhard Senft
  • Patent number: 6448220
    Abstract: The novel ketones having the structure in which R is H or an alkyl group and X is a hydrocarbon group having between 4 and 12 carbon atoms, the ring being saturated or unsaturated, excluding 4-(1-ethylpropylidene)-1-cyclohexanone, 4-cyclohexylidene-1-cyclohexanone, 4-butylidene-1-cyclohex-2-enone, 4-(1-ethylpropylidene)-1-cyclohex-2-enone, 4-(2-methylpropylidene)-1-cyclohexanone, 4-cyclohexyliden-2-cyclohexen-1-one, 4-(1,5-dimethyl-4-hexenylidene)-1-cyclohexanone, 4-[4-(cyclohexyliden)cyclohexyliden]-1-cyclohexanone, 4-[4-(tert-butyl)cyclohexyliden]-1-cyclohexanone, 4-[-(cyclohexyl)cyclohexyliden]-1-cyclohexanone, 4-(2-isopropyl-5-methylcyclohexyliden)-2-cyclohexen-1-one and 4-(3-phenylpropylidene)-1-cyclohex-2-enone exhibit interesting odor characteristics, generally aldehydic in nature, and so find use in perfumes and in perfumed products.
    Type: Grant
    Filed: March 30, 1999
    Date of Patent: September 10, 2002
    Assignee: Quest International B.V.
    Inventor: Karl Andrew Dean Swift
  • Publication number: 20020055453
    Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.
    Type: Application
    Filed: August 2, 2001
    Publication date: May 9, 2002
    Inventors: Marcus Eh, Ingo Wohrle
  • Publication number: 20020055454
    Abstract: The present invention is directed to the use of insoluble acesulfame in creating fragrances and scents in such items as perfumes, colognes, toilet waters, cleaning products and personal care products.
    Type: Application
    Filed: November 14, 2001
    Publication date: May 9, 2002
    Inventors: Richard M. Boden, Charles E.J. Beck
  • Patent number: 6319889
    Abstract: The invention is directed to novel compounds selected from the class of compounds having the structural formulae wherein the cyclohexane moiety with the dotted circle represents either a cyclohexane ring or a benzene ring, n represents an integer with the value 1, 3, or 4, m represents an integer with the value 1 or 2, R1, R2, R3, R4 and R5, represent hydrogen or a lower alkyl group, and the total carbon number of R1, R2, R3, R4 and R5, combined is eight or less.
    Type: Grant
    Filed: July 23, 1999
    Date of Patent: November 20, 2001
    Assignee: PFW Aroma Chemicals B.V.
    Inventors: Willem Lenselink, Anton Pieter Johan van Manen
  • Patent number: 6313087
    Abstract: Perfumes and perfumed products comprising 3-alkylcycloalkan-1-ols of formula (I), wherein R1 represents hydrogen or a methyl, ethyl or propyl group; R2, R4 and R5 independently represent hydrogen or a methyl group; R3 represents a saturated hydrocarbon group with 4-8 carbon atoms, provided that the first carbon atom of this hydrocarbon group is not a tertiary carbon atom, and n represents the numbers 1, 2 and 3. The invention also concerns compounds of formula (I) wherein R1 represents a methyl, ethyl or propyl group and R2-R5 are as outlined above.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: November 6, 2001
    Assignee: Quest International BV
    Inventor: Karen Jane Rossiter
  • Patent number: 6187727
    Abstract: The use of 2-methyl-3-cyclohexylpropanol, esters thereof or mixtures thereof as fragrance materials is disclosed. The subject materials possess unique fragrance notes and are cost-effective materials. The esters are novel compounds.
    Type: Grant
    Filed: July 12, 1999
    Date of Patent: February 13, 2001
    Assignee: Bush Boake Allen, Inc.
    Inventors: Alex R. Pagano, Walter C. Frank
  • Patent number: 6184419
    Abstract: The present invention relates to new &agr;,&bgr;-unsaturated ketones of formula I. The new compounds exhibit an intense, very long lasting green galbanum-type odor with fruity undertones. Compositions containing these novel compounds are also provided.
    Type: Grant
    Filed: May 10, 2000
    Date of Patent: February 6, 2001
    Assignee: Givaudan Roure (International) SA
    Inventors: Katja Berg-Schultz, Jerzy A. Bajgrowiecz
  • Patent number: 6177400
    Abstract: The compounds according to the general formula in which formula the dotted lines indicate a single or a double bond, n and m are 0 or 1, R1 is hydrogen or an acyl group —C(O)R3, R3 being a linear or branched alkyl or alkylene group from C1 to C8, the oxygen atom being bound to the adjacent &agr;-carbon atom by a double bond in the case where n is 0 and by a single bond in the case where n is 1, R2 is hydrogen or a linear or branched alkyl, alkenyl or alkoxy group from C1 to C8, or R2 is an alkenoxy group which is linked to the group R1 to form a 1,3-dioxolane cycle having 5 to 7 ring members, are useful perfuming ingredients. The most preferred compounds according to the invention are those which have a damascone- or damascenone-like structure, with the methyl substituent being in 4-position of the ring instead of the 2-position, as is the case in damascones and damascenones.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: January 23, 2001
    Assignee: Firmenich SA
    Inventors: Hubert Mimoun, Wolfgang Klaus Giersch
  • Patent number: 6172016
    Abstract: The use of 3-methyl-5-cyclohexylpentanol, 3-methyl-5-cyclohexylpentanal or mixtures thereof as fragrance materials is disclosed. The subject materials possess unique fragrance notes and are advantageous in that they are cost-effective.
    Type: Grant
    Filed: July 12, 1999
    Date of Patent: January 9, 2001
    Assignee: Bush Boakes Allen Inc.
    Inventors: Alex R. Pagano, Walter C. Frank
  • Patent number: 6054426
    Abstract: The optically active compounds of formula ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl radical, or of formula ##STR2## are useful as perfuming ingredients for the preparation of perfuming compositions and perfumed articles to which they impart woody-amber notes.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: April 25, 2000
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Christian Margot, Christian Chapuis, Dana Philip Simmons, Daniel Reichlin
  • Patent number: 6051548
    Abstract: Described are trimethylcyclohexenylcyclopropyl ketones having the structure: ##STR1## wherein one of the dashed lines is a carbon--carbon double bond and the other of the dashed lines is a carbon--carbon single bond, uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles, and mixtures of same with 3-methyl-1-phenylpentanol-5 and/or butanoylcyclohexane derivatives and/or acetic or propionic acid esters of o-methylphenyl isopropanol.
    Type: Grant
    Filed: November 5, 1998
    Date of Patent: April 18, 2000
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna
  • Patent number: 6025323
    Abstract: The compounds of formula ##STR1## in which R stands for a methyl or ethyl group, are used as perfume ingredients for the preparation of perfuming compositions and perfumed articles, to which they confer aromatic and thujonic notes. The compounds can be used in the form of a mixture of enantiomers or in an enantiomerically pure state. The invention also comprises original processes for the preparation of these compounds.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: February 15, 2000
    Assignee: Firmenich SA
    Inventors: Charles Fehr, Christian Margot
  • Patent number: 5939368
    Abstract: The use of 1-methoxy-2-methyl-3-phenylpropane, 3-methoxy-2,2,3-trimethyl-1-phenylbutane or of 1-(2-methoxypropyl)-4-methylbenzene as perfuming ingredients is described. These two compounds possess an excellent stability in aggressive media and/or at high pH-values, which renders them very useful for application in chlorine bleach. The odor of these two compounds can be described as being of the green type with a nice, strong floral note.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: August 17, 1999
    Assignee: Firmenich SA
    Inventors: Herve Pamingle, Jean-Marc Gaudin
  • Patent number: 5888962
    Abstract: The present invention relates to a perfumery material composed of a mixture of 3-methyl-5-phenyl-pentanenitrile and 3-methyl-5-cyclohexyl-pentanenitrile, which can be combined with other perfumery materials.
    Type: Grant
    Filed: November 20, 1997
    Date of Patent: March 30, 1999
    Assignee: Bush Boake Allen Inc.
    Inventors: Walter C. Frank, Alex R. Pagano
  • Patent number: 5821380
    Abstract: Novel 2-cyanoacrylic esters I ##STR1## where the radicals have the following meanings: R.sup.1 and R.sup.2 are each hydrogen or a radical having an iso- or heterocyclic ring system with at least one iso- or heteroaromatic nucleus, and at least one of the radicals R.sup.1 or R.sup.2 must be different from hydrogen,n is from 2 to 10, andX is, when n=2, a radical of the formula II ##STR2## where m is from 2 to 8, and X is, when n>2, the radical of an n-hydric aliphatic or cycloaliphatic polyol having 3-20 carbon atoms, it also being possible for a cycloaliphatic radical to contain 1 or 2 hetero atoms, and for an aliphatic radical to be interrupted by up to 8 non-adjacent oxygen atoms, sulfur atoms, imino or C.sub.1 -C.sub.4 -alkylimino groups, are used as light stabilizers.
    Type: Grant
    Filed: May 12, 1997
    Date of Patent: October 13, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Holderbaum, Alexander Aumuller, Hubert Trauth, Guido Voit, Karin Sperling, Alfred Krause
  • Patent number: 5798385
    Abstract: Described is a composition which is both an insect repellent and a perfume containing:Para-isopropylcyclohexanol;3,7-dimethyl-2,6-octadien-1-al;5,9-dimethyl-4,8-decadienal;p-mentha-1,8-diene;o-methyl-betaphenylethyl alcohol; and4-cyclooctenyl methyl carbonate.Also described is a method of using such formulation in order to repel insects.
    Type: Grant
    Filed: August 21, 1997
    Date of Patent: August 25, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Anna Belle Marin
  • Patent number: 5767305
    Abstract: Described are cyclopropyl carboxylic acid esters defined according to the structure: ##STR1## or the structure: ##STR2## wherein R.sub.1 is cis-3-hexenyl or cyclohexyl methyl and R.sub.2 is one of n-hexyl, cis-3-hexenyl, cyclohexyl methyl or n-heptyl and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles. The compounds having the structure: ##STR3## are novel compounds.
    Type: Grant
    Filed: April 3, 1997
    Date of Patent: June 16, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Gail I. Malcolm, Marie R. Hanna, Marc D. Evans
  • Patent number: 5731283
    Abstract: Described are 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrogen or methyl; wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond; wherein the wavy line represents a carbon carbon single bond or a carbon carbon double bond; with the proviso that when the wavy line is a carbon carbon single bond then the dashed line is a carbon carbon single bond; wherein Y represents a moiety selected from the group consisting of: ##STR2## wherein H represents hydrogen, C.sub.1 -C.sub.4 lower alkyl or C.sub.1 -C.sub.2 acyl; and wherein R.sub.1 represents C.sub.1 -C.sub.4 lower alkyl with the additional proviso that when Y is the moiety: ##STR3## then the dashed line is a carbon carbon single bond, and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles and colognes.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: March 24, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, James Joseph Koestler, Jan Van Elst
  • Patent number: 5707612
    Abstract: This disclosure introduces the use of an isophorone diisocyanate urethane polymer of naturally occurring castor oil as an active ingredient for skin and personal care compositions and products.
    Type: Grant
    Filed: April 8, 1996
    Date of Patent: January 13, 1998
    Assignee: Alzo, Inc.
    Inventors: Albert Zofchak, John Obeji, Michael Mosquera
  • Patent number: 5525589
    Abstract: The present invention is concerned with novel odorant compositions which are characterized by a content of cyclic compounds of the formula ##STR1## From this group of compounds the compounds I' with the meanings b), d), f) and g) are novel compounds.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: June 11, 1996
    Assignee: Givaudan-Roure Corporation
    Inventors: Franz Etzweiler, Daniel Helmlinger
  • Patent number: 5432154
    Abstract: The invention relates to novel ethers and their use as aroma precursors. The ethers are derived from ionol and related compounds. These aroma precursors do not have a substantial aroma as such under ambient conditions, but will break up into a complex mixture having useful organoleptic properties under heating. The ethers are especially suitable for use in products which are heated, burned or smouldered in some stage of their use. The compounds according to the invention are especially suitable for application to tobacco. Mixtures obtained by degrading (e.g. by heating) the ethers according to the invention may be used in a flavoring or perfuming mixture as well due to their organoleptic properties.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: July 11, 1995
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Johannes T. de Heij, Franciscus P. van Lier, Harrie Renes
  • 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: 5326748
    Abstract: The invention relates to compounds of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines. Compounds (I) are useful as perfuming ingredients for the preparation of perfuming compositions and perfuming articles, to which they impart sandalwood-animal notes.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: July 5, 1994
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Patent number: 5313002
    Abstract: The invention relates to novel ethers and their use as aroma precursors. The ethers are derived from ionol and related compounds. These aroma precursors do not have a substantial aroma as such under ambient conditions, but will break up into a complex mixture having useful organoleptic properties under heating. The ethers are especially suitable for use in products which are heated, burned or smouldered in some stage of their use. The compounds according to the invention are especially suitable for application to tobacco. Mixtures obtained by degrading (e.g. by heating) the ethers according to the invention may be used in a flavouring or perfuming mixture as well due to their organoleptic properties.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: May 17, 1994
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Johannes T. De Heij, Franciscus P. Van Lier, Harrie Renes
  • Patent number: 5250512
    Abstract: An optically active 3-[6(S)-2,2,6-trimethylcyclohexan-1-yl]propanol derivative represented by formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group, and a perfume containing the same as an active ingredient are disclosed.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: October 5, 1993
    Assignee: Takasago International Corporation
    Inventors: Tatsuya Ohmoto, Akemi Shimada, Takeshi Yamamto
  • Patent number: 5240907
    Abstract: Described are substituted cyclopentyl oxabicyclooctanes, cyclopentyl vinyl pyrans, cyclopentylformylcyclohexenes and cyclopentylhydroxymethyl cyclohexenes having the generic structures: ##STR1## wherein R.sub.1, R.sub.2, R', R", R.sub.1 ', R.sub.2 ', R.sub.1 " and R.sub.2 " represent hydrogen or methyl with the provisos that:(i) R.sub.1 and R.sub.2 are not both methyl;(ii) R' and R" are not both methyl;(iii) when R.sub.1 ' is methyl, R.sub.2 ' is hydrogen; and(iv) when R.sub.2 " is methyl, then R.sub.1 " is hydrogen,processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: August 31, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Franc T. Schiet, Charles E. J. Beck, Charles J. Vinals, Marie R. Hanna
  • Patent number: 5234902
    Abstract: Described are alpha,3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition having from about 85 up to about 90% by weight of a compound having the structure: ##STR1## and from about 10 up to about 15% by weight of a compound having the structure: ##STR2## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is hydrogen or acetyl with the proviso that when R.sub.1 is methyl, R.sub.2 is hydrogen; and uses thereof in augmenting or enhancing the aroma of 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; as well as processes for preparing said alpha,3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition.
    Type: Grant
    Filed: July 28, 1992
    Date of Patent: August 10, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Anthony T. Levorse, Jr.
  • 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: 5137741
    Abstract: Described is the use in augmenting or enhancing the aroma or taste of a foodstuff of a reaction product of linalool with citric acid wherein the reaction is carried out at 100.degree. C. in aqueous media for a period of from about two up to four hours. The resulting reaction product contains a novel mixture of terpenes.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: August 11, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael J. Zampino, Braja D. Mookherjee
  • Patent number: 5118865
    Abstract: Novel compounds of formula ##STR1## wherein the dotted lines indicate the location of a single or double bond, symbol R.sup.1 stands for a hydrogen atom or a methyl radical, symbol R.sup.2 represents a linear or branched, saturated or unsaturated, C.sub.1 to C.sub.4 alkyl radical, provided that R.sup.1 is not hydrogen when R.sup.2 represents a methyl or n-propyl radical and the ring is saturated. Compounds (Ia) are useful as perfuming ingredients.A process for their preparation is disclosed.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: June 2, 1992
    Assignee: Firmenich SA
    Inventors: Christian Chapuis, Karl-Heinrich Schulte-Elte, Herve Pamingle, Christian Margot
  • Patent number: 5104851
    Abstract: A 2-(alkyl-cyclohexyl)-1-propanol is disclosed. The compound is represented by formula (I): ##STR1## wherein R.sub.1 and R.sub.2 individually represent a group selected from the members consisting of methyl-, ethyl-, n-propyl-, i-propyl-, t-butyl-, and sec-butyl groups, provided that the total carbon atoms of the R.sub.1 and R.sub.2 groups are 4 to 7; either R.sub.1 and R.sub.2 is a hydrogen atom, the other being a cyclohexyl group; or R.sub.1 and R.sub.2 together form a hexamethylene ring together with 2 carbon atoms in the cyclohexane ring. The compound possesses a long-lasting, woody, floral odor, and can be widely used as perfumery materials such as perfumes, soaps, shampoos, aromatic goods, and detergents.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: April 14, 1992
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Hiroaki Ohnuma, Manabu Fujita, Nao Toi
  • Patent number: 5100872
    Abstract: Described are alkyl cyclohexylmethyl and cyclohexenylmethyl carbonates defined according to the generic structure: ##STR1## wherein R.sub.1 is methyl or ethyl; R.sub.2, R.sub.3, R.sub.4 and R.sub.6 represents hydrogen or methyl; R.sub.5 represents hydrogen, methyl or methylene; and R.sub.7 represents hydrogen or C.sub.1 -C.sub.4 straight chain lower alkyl or isopropyl or R.sub.7 is no moiety; each of the dashed lines represents a carbon-carbon single bond or a carbon-carbon double bond; the wavy line represents a carbon-carbon single bond or no bond; with the provisos that:(a) at least three of the dashed lines each represents a carbon-carbon single bond;(b) when R.sub.7 is no moiety, the dashed line at the "1-6" position is a carbon-carbon double bond;(c) when the wavy line is a carbon-carbon single bond then R.sub.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: March 31, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Leroy John, Anton V. Ouwerkerk, Vincent F. Kuczinski, Sophia Grojsman
  • Patent number: 5098886
    Abstract: Described are alkyl cyclohexylmethyl and cyclohexenylmethyl carbonates defined according to the structure: ##STR1## wherein R.sub.1 is methyl or ethyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.6 are the same or different hydrogen or methyl and wherein the dashed line is a carbon-carbon single bond or a carbon-carbon double bond and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, hair sprays, shampoos, bath oils and perfumed polymers.
    Type: Grant
    Filed: March 17, 1991
    Date of Patent: March 24, 1992
    Inventors: Anubhav P. S. Narula, Leroy John, Anton V. Ouwerkerk, Vincent F. Kuczinski, Sophia Grojsman
  • Patent number: 5089469
    Abstract: Described are isomeric mixtures of bisabolene prepared by dehydrating nerolidol using citric acid or phosphoric acid and then distilling the resulting product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing natural, dry, floral, opoponax aromas with floral, freesia, fruity, citrus, bergamot, mango and opoponax topnotes in perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic, or zwitterionic detergents, fabric softener compositions, drier-added fabric softener articles, cosmetic powders and the like; and useful for repelling specific species of insects, namely, house flies Musca domestica L. (Diptera Muscidae)) and the species of mosquitoes, Aedes aegypti.
    Type: Grant
    Filed: April 25, 1991
    Date of Patent: February 18, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael J. Zampino, Richard A. Wilson, Braja D. Mookherjee
  • Patent number: 5070073
    Abstract: Described are cyclopentenyl-oxabicyclooctanes, cyclopentenyl-formylcyclohexenes and cyclopentyl-hydroxymethyl cyclohexenes having the generic structures: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 ', and R.sub.3 " each represents hydrogen or methyl with the provisos:(i) one or two of R.sub.1, R.sub.2, R.sub.3 ' and R.sub.3 " represents methyl;(ii) R.sub.1 and/or R.sub.2 are methyl;(iii) at least one of R.sub.3 ' and R.sub.3 " is hydrogen; and(iv) when R.sub.1 and R.sub.2 is methyl then each of R.sub.3 ' and R.sub.3 " is hydrogenwherein R.sub.4 ' is hydrogen or C.sub.1 -C.sub.5 alkyl, processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.
    Type: Grant
    Filed: April 11, 1991
    Date of Patent: December 3, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Carlos Benaim, Anton V. Ouwerkerk, Olivier Gillotin
  • Patent number: 5068452
    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) posses 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: April 2, 1990
    Date of Patent: November 26, 1991
    Assignee: Firmenich SA
    Inventors: Ferdinand Naef, Francois Delay, Arnoldus Uijttewaal
  • Patent number: 5066639
    Abstract: Described are cyclohexenylmethyloxabicyclooctanes defined according to the generic structures: ##STR1## as well as intermediates for producing same defined according to the generic structures: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 ', and R.sub.3 " are each hydrogen or methyl with the provisos:(i) one or both of R.sub.1 and R.sub.2 is methyl;(ii) when R.sub.1 and R.sub.2 are both methyl then R.sub.3 ' and R.sub.3 " each represents hydrogen;(iii) one of R.sub.3 ' and R.sub.3 " is methyl and the other is hydrogen or R.sub.3 ' and R.sub.3 " both represent hydrogen; and(iv) when R.sub.3 ' and R.sub.3 " are both methyl then R.sub.1 is methyl and R.sub.2 is hydrogen;and R.sub.4 ' is hydrogen or C.sub.1 -C.sub.5 alkyl. Also described are the organoleptic uses of said cyclohexenylmethyloxabicyclooctanes wherein implementing or enhancing the aroma of perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: April 11, 1991
    Date of Patent: November 19, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. DeVirgilio
  • Patent number: 5049544
    Abstract: Disclosed is a perfumery composition comprising a 2-cyclohexylpropionic acid or its derivative represented by the following formula (I): ##STR1## wherein R is a hydrogen atom, an alkyl group having 1-4 carbon atoms, or an alkenyl group having 2-4 carbon atoms.The compounds have a wide variety of odors and a wide application as perfumery compositions such as high-grade perfumery compositions, perfumes, soaps, shampoos, rinses, detergents, cosmetics, sprays, room fragrances, and the like.
    Type: Grant
    Filed: July 27, 1990
    Date of Patent: September 17, 1991
    Assignee: Kao Corporation
    Inventors: Junji Koshino, Yoshiaki Fujikura, Nao Toi
  • Patent number: 4978653
    Abstract: 2-Cyclohexylpropanal derivatives are disclosed. The derivatives are represented by the following formula (I): ##STR1## wherein P is a hydrogen atom and Q represents a group --CH.dbd.N--OH or a group --CH(OR).sub.2, wherein each R represents a lower alkyl group or two R's together form a lower alkylene group which may have a lower alkyl substituent, or P and Q together form a group ##STR2## wherein R' is a lower alkyl group. The compounds possess floral, fruity, or green odors and are useful for preparing perfume compositions.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: December 18, 1990
    Assignee: Kao Corporation
    Inventors: Junji Koshino, Yoshiaki Fujikura, Manabu Fujita, Nao Toi
  • Patent number: 4960946
    Abstract: The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: ##STR1## wherein A is ##STR2## and wherein R.sub.1 is methyl or ethyl, R.sub.2 -R.sub.7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R.sub.2 -R.sub.7 are methyl, and R.sub.8 is hydrogen, lower alkyl (C.sub.1 to C.sub.5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF K&F
    Inventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
  • Patent number: 4956342
    Abstract: Multimethyl cyclohexene or cyclohexane derivatives having woody, spicy, amber or violet odors are disclosed. The derivatives can be formualted into perfumes, talcs, lotions, cremes and air fresheners.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: September 11, 1990
    Assignee: BASF K & F Corp.
    Inventors: Philip A. Christenson, Brian J. Drake
  • 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: RE37159
    Abstract: An optically active 3-[6(S)-2,2,6-trimethylcyclohexan-1-yl]propanol derivative represented by formula (I): wherein R1 represents a lower alkyl group, and a perfume containing the same as an active ingredient are disclosed.
    Type: Grant
    Filed: July 8, 1998
    Date of Patent: May 1, 2001
    Assignee: Takasago International Corporation
    Inventors: Tatsuya Ohmoto, Akemi Shimada, Takeshi Yamamoto