Cyano Containing Active Ingredient Patents (Class 512/6)
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Patent number: 6867175Abstract: 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: GrantFiled: April 28, 2001Date of Patent: March 15, 2005Assignee: Kao CorporationInventors: Thomas Markert, Theo Ten Pierik, Werner Faber
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Publication number: 20040127394Abstract: The novel substance 5,7,7-trimethyloctanenitrile and certain uses of this substance, in particular as a fragrance, are described.Type: ApplicationFiled: October 14, 2003Publication date: July 1, 2004Inventors: Johannes Panten, Karl-Georg Fahlbusch, Mathias Werner, Pascal Sillon
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Patent number: 6743768Abstract: 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: GrantFiled: July 20, 2001Date of Patent: June 1, 2004Assignee: Givaudan SAInventors: Markus Gautschi, Jean-Pierre Bachmann
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Publication number: 20030153485Abstract: 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: ApplicationFiled: April 15, 2003Publication date: August 14, 2003Inventors: Thomas Markert, Theo Ten Pierik, Werner Faber
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Publication number: 20030069167Abstract: The present invention relates to the use as a perfuming ingredient of 2-methyl-3-hexanone-oxime of formula 1Type: ApplicationFiled: August 19, 2002Publication date: April 10, 2003Inventors: Pierre-Alain Blanc, Piero Fantini, Peter Fankhauser
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Patent number: 6410504Abstract: 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: GrantFiled: November 28, 2000Date of Patent: June 25, 2002Assignee: Firmenich, SAInventor: Wolfgang Giersch
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Patent number: 6310033Abstract: 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: GrantFiled: December 28, 1999Date of Patent: October 30, 2001Assignee: Bush Boake Allen Inc.Inventors: Alex R. Pagano, Walter C. Frank, Vrej Jubian
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Patent number: 6310032Abstract: 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: GrantFiled: March 2, 2000Date of Patent: October 30, 2001Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna, Charles E. J. Beck
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Patent number: 6180814Abstract: 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: GrantFiled: November 4, 1998Date of Patent: January 30, 2001Assignee: Firmenich SAInventor: Wolfgang Giersch
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Patent number: 5888962Abstract: 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: GrantFiled: November 20, 1997Date of Patent: March 30, 1999Assignee: Bush Boake Allen Inc.Inventors: Walter C. Frank, Alex R. Pagano
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Patent number: 5696075Abstract: 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: GrantFiled: July 27, 1995Date of Patent: December 9, 1997Assignee: Firmenich SAInventors: Christian Chapuis, Pierre-Alain Blanc
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Patent number: 5618784Abstract: 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: GrantFiled: September 26, 1995Date of Patent: April 8, 1997Assignee: Quest International B.V.Inventor: Paul N. Davey
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Patent number: 5525589Abstract: 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: GrantFiled: February 18, 1994Date of Patent: June 11, 1996Assignee: Givaudan-Roure CorporationInventors: Franz Etzweiler, Daniel Helmlinger
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Patent number: 5521151Abstract: 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: GrantFiled: December 29, 1994Date of Patent: May 28, 1996Assignee: Firmenich S.A.Inventors: Charles Fehr, Francois Delay, Pierre-Alain Blanc, Nathalie Chaptal-Gradoz
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Patent number: 5389608Abstract: 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: GrantFiled: May 12, 1994Date of Patent: February 14, 1995Assignee: International Flavors & Fragrances Inc.Inventors: Anthony T. Levorse, Marie R. Hanna, Charles E. J. Beck, Kathleen E. Boardwick
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Patent number: 5346884Abstract: 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: GrantFiled: October 1, 1993Date of Patent: September 13, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Charles E. J. Beck, Marie R. Hanna, Franc T. Schiet
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Patent number: 5300488Abstract: 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: GrantFiled: July 16, 1993Date of Patent: April 5, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Charles E. J. Beck, Marie R. Hanna, Jan T. Van Elst
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Patent number: 5294602Abstract: 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: GrantFiled: November 20, 1991Date of Patent: March 15, 1994Inventors: Ernst-Joachim Brunke, Karl-Georg Fahlbusch
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Patent number: 5236897Abstract: 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: GrantFiled: January 8, 1993Date of Patent: August 17, 1993Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber
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Patent number: 5212153Abstract: 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: GrantFiled: April 2, 1992Date of Patent: May 18, 1993Assignee: Haarmann & Reimer GmbHInventors: Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
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Patent number: 5204322Abstract: 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: GrantFiled: December 31, 1991Date of Patent: April 20, 1993Assignee: Union Camp CorporationInventor: Walter C. Frank
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Process for preparing phenyl butyronitriles and perfumery use of 2,2-dimethyl-4-phenyl valeronitrile
Patent number: 5179222Abstract: 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: GrantFiled: March 27, 1992Date of Patent: January 12, 1993Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber -
Process for preparing phenyl butyronitriles and perfumery use of 2,2-dimethyl-4-phenyl valeronitrile
Patent number: 5143899Abstract: 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: GrantFiled: September 13, 1991Date of Patent: September 1, 1992Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber -
Patent number: 5105005Abstract: 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: GrantFiled: September 12, 1990Date of Patent: April 14, 1992Assignee: Haarmann & Reimer GmbHInventors: Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
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Patent number: 5075489Abstract: 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: GrantFiled: April 25, 1990Date of Patent: December 24, 1991Assignee: BASF AktiengesellschaftInventors: Gerald Lauterbach, Rainer Becker, Klaas Jansen
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Patent number: 4990494Abstract: 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: GrantFiled: February 2, 1990Date of Patent: February 5, 1991Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Eleanor Fox
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Patent number: 4985402Abstract: 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: GrantFiled: April 25, 1990Date of Patent: January 15, 1991Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, De Virgilio John J.
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Patent number: 4983579Abstract: Described are cyano-substituted sulfur-containing compounds having the structures: ##STR1## as well as organoleptic uses thereof.Type: GrantFiled: June 29, 1990Date of Patent: January 8, 1991Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Joseph A. McGhie
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Patent number: 4962089Abstract: 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: GrantFiled: October 20, 1989Date of Patent: October 9, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Joseph A. McGhie
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Patent number: 4912088Abstract: 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: GrantFiled: August 5, 1988Date of Patent: March 27, 1990Assignee: Draggo Gerberding & Co.Inventors: Ernst-Joachim Brunke, Claus-Hermann Kappey
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Patent number: 4883884Abstract: 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: GrantFiled: November 18, 1988Date of Patent: November 28, 1989Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Joseph A. McGhie
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Patent number: 4863631Abstract: 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: GrantFiled: June 24, 1988Date of Patent: September 5, 1989Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Margo Androulakis
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Patent number: 4837351Abstract: 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: GrantFiled: December 2, 1987Date of Patent: June 6, 1989Assignee: Kuraray Company Ltd.Inventors: Masahiro Torihara, Yoshin Tamai
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Patent number: 4755615Abstract: 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: GrantFiled: January 10, 1985Date of Patent: July 5, 1988Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Slagmulder Andre
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Patent number: 4722808Abstract: 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: GrantFiled: April 29, 1986Date of Patent: February 2, 1988Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Andre Slagmulder