Cyano Containing Active Ingredient Patents (Class 512/6)
  • Patent number: 6867175
    Abstract: A Compound corresponding to formula (I): wherein X is a group selected from the group consisting of —CHO, —CN, —CH?NOH, and —CH2OH, and wherein the C?C double bond assumes a Z or E configuration.
    Type: Grant
    Filed: April 28, 2001
    Date of Patent: March 15, 2005
    Assignee: Kao Corporation
    Inventors: Thomas Markert, Theo Ten Pierik, Werner Faber
  • Publication number: 20040127394
    Abstract: The novel substance 5,7,7-trimethyloctanenitrile and certain uses of this substance, in particular as a fragrance, are described.
    Type: Application
    Filed: October 14, 2003
    Publication date: July 1, 2004
    Inventors: Johannes Panten, Karl-Georg Fahlbusch, Mathias Werner, Pascal Sillon
  • Patent number: 6743768
    Abstract: The present invention relates to a fragrance composition containing a mixture of (9E)-undecenonitrile, (9Z)-undecenonitrile, and 10-undecenonitrile, which can be combined with additional fragrance ingredients, and which is useful in perfumery, and a process of preparing a scented consumer product using the composition.
    Type: Grant
    Filed: July 20, 2001
    Date of Patent: June 1, 2004
    Assignee: Givaudan SA
    Inventors: Markus Gautschi, Jean-Pierre Bachmann
  • Publication number: 20030153485
    Abstract: Compounds of general formula (I), where X═ a CHO, CN, CH═NOH, or CH2OH group and the C═C double bond may be either E or Z configuration are characterised by an interesting and original odour characteristic with high dispersion. Said compounds are suitable for use as fragrances, for example in cosmetic preparations, technical products or in alcoholic perfumery.
    Type: Application
    Filed: April 15, 2003
    Publication date: August 14, 2003
    Inventors: Thomas Markert, Theo Ten Pierik, Werner Faber
  • Publication number: 20030069167
    Abstract: The present invention relates to the use as a perfuming ingredient of 2-methyl-3-hexanone-oxime of formula 1
    Type: Application
    Filed: August 19, 2002
    Publication date: April 10, 2003
    Inventors: Pierre-Alain Blanc, Piero Fantini, Peter Fankhauser
  • Patent number: 6410504
    Abstract: The compounds of formula in which X is a C≡N group or a C(H)═O group and the C5-ring is either saturated or carries a double bond in one of the positions indicated by the dotted lines, or any mixture of two or more compounds of formula (I), are described. The compounds and mixtures were found to be useful as perfuming ingredients, with the compounds of the above formula in which X is a C≡N group and the C5-ring has a double bond in one of the positions indicated by the dotted lines, being particularly stable in aggressive media. The odor note of these compounds is quite close to that of citral, i.e. of the fresh-citrus type with green and lime connotations.
    Type: Grant
    Filed: November 28, 2000
    Date of Patent: June 25, 2002
    Assignee: Firmenich, SA
    Inventor: Wolfgang Giersch
  • Patent number: 6310033
    Abstract: The use of substituted 5-phenylpentan-1-ols, 5-phenylpentanals, 5-phenylpentanitriles, 5-phenylpentanoic acid and lower alkyl esters thereof and 5-phenylpentanyl esters of C1-C6 aliphatic acids as fragrance materials is disclosed. The subject fragrance materials are, in large measure, novel compounds. The subject materials possess unique fragrance notes and are cost-effective materials.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: October 30, 2001
    Assignee: Bush Boake Allen Inc.
    Inventors: Alex R. Pagano, Walter C. Frank, Vrej Jubian
  • Patent number: 6310032
    Abstract: Described are &agr;-oxygen-substituted cyclohexane propionitriles having the structure: wherein R20 and R21 are the same or different C1-C3 lower alkoxy; or wherein R20 is hydrogen and R21 is hydroxy, C1-C3 lower alkoxy or C1-C3 lower acyloxy; and wherein R1, R2, R3, R4, R5, R6 and R7 are the same or different hydrogen or C1-C4 lower alkyl, and uses thereof for their organoleptic properties in augmenting or enhancing or imparting aromas in or to perfume compositions, colognes, microporous polymers or perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair care compositions and the like.
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: October 30, 2001
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna, Charles E. J. Beck
  • Patent number: 6180814
    Abstract: The compounds of formula in which X is a C≡N group or a C(H)═O group and the C5-ring is either saturated or carries a double bond in one of the positions indicated by the dotted lines, or any mixture of two or more compounds of formula (I), are described. The compounds and mixtures were found to be useful as perfuming ingredients, with the compounds of the above formula in which X is a C≡N group and the C5-ring has a double bond in one of the positions indicated by the dotted lines, being particularly stable in aggressive media. The odor note of these compounds is quite close to that of citral, i.e. of the fresh-citrus type with green and lime connotations.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: January 30, 2001
    Assignee: Firmenich SA
    Inventor: Wolfgang Giersch
  • 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: 5696075
    Abstract: Described herein are compounds of the formula ##STR1## wherein R represents a hydrogen atom or a methyl radical and X stands for a --CHO, or a --CN group, are useful as perfuming ingredients for preparing perfuming compositions and a variety of perfumed articles, to which they impart sandalwood-type odor notes, together with marine, ozone type odor characters, such that said compositions and articles thus acquire a "transparent" connotation. The aldehydes of formula (I) are also useful as starting products for the preparation of the corresponding fragrant alcohols and nitriles.
    Type: Grant
    Filed: July 27, 1995
    Date of Patent: December 9, 1997
    Assignee: Firmenich SA
    Inventors: Christian Chapuis, Pierre-Alain Blanc
  • Patent number: 5618784
    Abstract: Novel compounds, 3-(2-methylbut-1-oxy)- and 3-(3-methylbut-1-oxy)-2-methylpropionitrile, use of these compounds as fragrance materials, and perfumes containing these compounds.
    Type: Grant
    Filed: September 26, 1995
    Date of Patent: April 8, 1997
    Assignee: Quest International B.V.
    Inventor: Paul N. Davey
  • 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: 5521151
    Abstract: We disclose a novel nitrile, i.e. 5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbonitrile, a perfuming ingredient having a musky, earthy odor, and which is remarkably stable in particularly aggressive media such as for instance antiperspirant bases. This compound may present itself as a racemate or in the form of one of its optically active isomers.Said isomers can be obtained from aldehydes, namely (-)-(6S,7S) and (+)-(6R,7R)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphtalenecarba ldehyde, which aldehydes are not only useful as starting products for the preparation of the corresponding nitriles, but also as perfuming ingredients.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: May 28, 1996
    Assignee: Firmenich S.A.
    Inventors: Charles Fehr, Francois Delay, Pierre-Alain Blanc, Nathalie Chaptal-Gradoz
  • Patent number: 5389608
    Abstract: Described are 1-phenyl-1-cyano-C.sub.5 -C.sub.7 alkanes defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 each represents hydrogen or methoxy with the proviso that when R.sub.1 is methoxy, R.sub.2 is hydrogen and when R.sub.2 is methoxy, R.sub.1 is hydrogen; and wherein X is C.sub.3 -C.sub.5 straight chain or branched chain alkylene and uses thereof in augmenting, enhancing or modifying perfume compositions, perfumed articles and colognes. Also described is a process for preparing such 1-phenyl-1-cyano-C.sub.5 -C.sub.7 alkanes by means of reacting benzyl cyanide with an aldehyde or ketone and then hydrogenating the resulting product using a supported palladium catalyst.
    Type: Grant
    Filed: May 12, 1994
    Date of Patent: February 14, 1995
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anthony T. Levorse, Marie R. Hanna, Charles E. J. Beck, Kathleen E. Boardwick
  • Patent number: 5346884
    Abstract: Described are substituted 2,6-dimethylbicyclo[3,3,1]-non-6-enes defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein "R" represents one of the moieties: ##STR2## 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).
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: September 13, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Charles E. J. Beck, Marie R. Hanna, Franc T. Schiet
  • Patent number: 5300488
    Abstract: Described are p-methylenedioxyphenyl propionitrile and propiohydroxylamine derivatives defined according to the generic structure: ##STR1## wherein Z.sub.1 represents the moiety: ##STR2## and the moiety: ##STR3## and R.sub.1 is hydrogen or methyl and also having the generic structure: ##STR4## wherein X is HSO.sub.3.sup.- ; SO.sub.4 ;=Cl.sup.- ; PO.sub.4.sup..tbd. ; H.sub.2 PO.sub.4.sup.- ; and HPO.sub.4.sup.=. The p-methylenedioxyphenyl propionitrile and propiohydroxylamine derivatives having the structures: ##STR5## have useful organoleptic properties in the perfumery area. Also described are processes for preparing such p-methylenedioxyphenyl propionitrile and propiohydroxylamine derivatives. The compounds defined according to the structure: ##STR6## are useful intermediates in such processes. The subgenus defined according to the structure: ##STR7## covers novel compounds.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: April 5, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Charles E. J. Beck, Marie R. Hanna, Jan T. Van Elst
  • Patent number: 5294602
    Abstract: The 3-(hexenyloxy)-propane-nitriles of general formula A, in which R.sup.1 and R.sup.2 are optionally a hydrogen atom or a methyl group and R.sup.3 is an unbranched hexenyl group, are new and are useful as odour materials such as ingredients for perfume compositions. Their production is carried out through the base catalysed addition of acrylonitrile or methyl substituted acrylonitrile to the unbranched hexenol, in which the reaction temperature is between 0.degree. and 50.degree. C. (for acrylonitrile especially between 0.degree. and 10.degree. C., for crotonitrile especially between 15.degree. and 25.degree. C. and for methacrylonitrile, especially between 30.degree. and 40.degree. C.), and the aforesaid base is benzyl trimethylammonium hydroxide (Triton B).
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: March 15, 1994
    Inventors: Ernst-Joachim Brunke, Karl-Georg Fahlbusch
  • Patent number: 5236897
    Abstract: Described are the 2,2-dimethyl-4(2' or 4'-pyridyl) butyronitriles defined according to the generic structure: ##STR1## wherein one of R.sub.1 ' or R.sub.2 ' is the moiety: ##STR2## and the other of R.sub.1 ' or R.sub.2 ' is hydrogen as well as perfumery uses thereof and processes for preparing same.
    Type: Grant
    Filed: January 8, 1993
    Date of Patent: August 17, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber
  • Patent number: 5212153
    Abstract: New nitriles which are odoriferous substances having an extremely fresh note are accessible by Knoevenagel condensation of 2-cyclopentyl-cyclopentanone and cyanoacetic acid and decarboxylation of the reaction product.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: May 18, 1993
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
  • Patent number: 5204322
    Abstract: The present invention relates to novel nitrile and aldoxime indane compounds, such as 1,1,2,3,3,4,6-heptamethylindane-5-nitrile and 1,1,2,3,3,4,6-heptamethylindane-5-aldoxime, and to compositions containing the same. Compounds and compositions of the invention possess a fragrant musk-like aroma, and thus are useful in the perfumery and/or other industries.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: April 20, 1993
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 5179222
    Abstract: Described is the use in imparting, augmenting or enhancing aromas to or in perfume compositions, colognes and perfumed articles by admixing therewith an aroma imparting, augmenting or enhancing quantity of 2,2-dimethyl-4-phenyl valeronitrile defined according to the structure: ##STR1## Also described herein is a process for preparing phenyl butyronitriles by reacting isobutyronitrile having the structure: ##STR2## with a styrene derivative defined according to the structure: ##STR3## according to the reaction: ##STR4## in the presence of a catalyst selected from the group consisting of sodium hydride and lithium diisopropyl amide having the structure: ##STR5## at a temperature in the range of from about 90.degree. C. up to about 130.degree. C. yielding more than about 65% by weight of product wherein R.sub.1 and R.sub.2 are the same or different and each represents hydrogen or methyl.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: January 12, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber
  • Patent number: 5143899
    Abstract: Described is the use in imparting, augmenting or enhancing aromas to or in perfume compositions, colognes and perfumed articles by admixing therewith an aroma imparting, augmenting or enhancing quantity of 2,2-dimethyl-4-phenyl valeronitrile defined according to the structure: ##STR1## Also described herein is a process for preparing phenyl butyronitriles by reacting isobutyronitrile having the structure: ##STR2## with a styrene derivative defined according to the structure: ##STR3## according to the reaction: ##STR4## in the presence of a catalyst selected from the group consisting of sodium hydride and lithium diisopropyl amide having the structure: ##STR5## at a temperature in the range of from about 90.degree. C. up to about 130.degree. C. yielding more than about 65% by weight of product wherein R.sub.1 and R.sub.2 are the same or different and each represents hydrogen or methyl.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: September 1, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber
  • Patent number: 5105005
    Abstract: The invention relates to new alkadienenitriles of the formula ##STR1## in which n is an integer from 5 to 9, a process for their preparation and their outstanding suitability as odororiferous substances.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: April 14, 1992
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
  • Patent number: 5075489
    Abstract: Unsaturated nitriles of the general formula I ##STR1## where R is a branched or straight-chain alkyl radical of 4 to 10 carbon atoms or a phenyl ring which is substituted by alkyl of 1 to 4 carbon atoms, one or more alkoxy groups of 1 to 3 carbon atoms, preferably 1 or 2 methoxy groups, or alkylenedioxy, preferably methylenedioxy, and their preparation and their use as scents.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: December 24, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerald Lauterbach, Rainer Becker, Klaas Jansen
  • 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: 4983579
    Abstract: Described are cyano-substituted sulfur-containing compounds having the structures: ##STR1## as well as organoleptic uses thereof.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: January 8, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Joseph A. McGhie
  • Patent number: 4962089
    Abstract: Described are cyano-substituted sulfur-containing compounds defined according to a structure selected from the group consisting of: ##STR1## wherein M is an alkali metal as well as uses of the nonionic structures of said group for their organoleptic properties.
    Type: Grant
    Filed: October 20, 1989
    Date of Patent: October 9, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Joseph A. McGhie
  • Patent number: 4912088
    Abstract: It has been found that .alpha.-campholenenitrile with formula A and .gamma.-campholenenitrile with formula B ##STR1## are excellent for use as fragrances, especially as components of fragrance mixtures for perfuming cosmetics or other consumer goods. The two nitriles can be used individually or in mixture with each other.
    Type: Grant
    Filed: August 5, 1988
    Date of Patent: March 27, 1990
    Assignee: Draggo Gerberding & Co.
    Inventors: Ernst-Joachim Brunke, Claus-Hermann Kappey
  • Patent number: 4883884
    Abstract: Described is the tetrahydro-5-isopropyl-2-methyl-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: November 18, 1988
    Date of Patent: November 28, 1989
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Joseph A. McGhie
  • Patent number: 4863631
    Abstract: Described are dimethyl substituted alkyl nitriles of our invention defined according to the generic structure: ##STR1## wherein N represents 0 or 1 and organoleptic 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 is a process for preparing such dimethyl substituted alkyl nitriles of our invention by means of reaction of aldehydes defined according to the structure: ##STR2## with hydroxylamine salts having the structure: ##STR3## wherein Y is an anion and P is 1 or 2 to form aldoximes defined according to the structure: ##STR4## The compounds defined according to the generic structure: ##STR5## are novel compounds.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: September 5, 1989
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Margo Androulakis
  • Patent number: 4837351
    Abstract: Described is a new chemical, 2-cyano-4-phenyl pentane, and the fragrance or perfume compositions containing said 2-cyano-4-phenyl pentane, in which the aroma of said 2-cyano-4-phenyl pentane is effectively imparted.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: June 6, 1989
    Assignee: Kuraray Company Ltd.
    Inventors: Masahiro Torihara, Yoshin Tamai
  • Patent number: 4755615
    Abstract: Cyclododecenylacetonitrile is prepared by reacting cyclododecanone with cyanoacetic acid in the presence of a catalyst. Purified cyclododecenylacetonitrile has a pleasant scent reminiscent of roses and lilies of the valley, containing additionally a musk note, and is suitable as a fragrance and as a fragrance component.
    Type: Grant
    Filed: January 10, 1985
    Date of Patent: July 5, 1988
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Slagmulder Andre
  • Patent number: 4722808
    Abstract: Cyclododecenylacetonitrile is prepared by reacting cyclododecanone with cyanoacetic acid in the presence of a catalyst. Purified cyclododecenylacetonitrile has a pleasant scent reminiscent of roses and lilies of the valley, containing additionally a musk note, and is suitable as a fragrance and as a fragrance component.
    Type: Grant
    Filed: April 29, 1986
    Date of Patent: February 2, 1988
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Andre Slagmulder