Patents Represented by Attorney Harold Haidt
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Patent number: 4108799Abstract: Described are hexahydrotetramethyl acetonaphthones and mixtures of such substituted acetonaphthones having the generic formula: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond, and, specifically, the novel isomer having the structure: ##STR2## and processes for the preparation of such mixtures and said novel isomer, as well as a known single component of said mixtures and compounds.The products produced are useful as vetiver ingredients in perfumes and perfumed articles.Type: GrantFiled: July 28, 1977Date of Patent: August 22, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, James N. Siano, Edward J. Shuster
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Patent number: 4107184Abstract: Novel 3-furyl alkyl disulfides having the formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.7 lower alkyl or C.sub.5 -C.sub.6 cycloalkyl; R.sub.2 and R.sub.3 are each selected from the group consisting of hydrogen and methyl, at least one of R.sub.2 and R.sub.3 being methyl provided that when R.sub.1 is methyl, each of R.sub.2 and R.sub.3 is methyl, such 3-furyl alkyl disulfides being useful in altering, modifying or enhancing the organoleptic properties of foodstuffs.Type: GrantFiled: October 7, 1975Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Howard H. Heinsohn, Jr., Manfred Hugo Vock
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Patent number: 4107093Abstract: Compositions are described for the use in perfume and cologne of the compound ##STR1## or of mixtures of the compounds ##STR2## to produce fruity, woody, piney aromas with armoise and floral nuances and slight chocolate undertones.Type: GrantFiled: July 28, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
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Patent number: 4107217Abstract: Described are intermediates, acetals formed in processes for producing novel 2-alkylidene-3-alkynals and 2-alkylidene-3-alkenals which processes comprise reacting an alkyl metallo acetylide with a dialkoxy acetonitrile or a dialkoxy dialkyl acetamide to form an imine salt, hydrolyzing the imine salt to form a 1,1-dialkoxy-3-alkyn-2-one, alternatively (a) first treating the alkynone with an alkylidene tri-substituted phosphorane or an alkylidene phosphorous triamide or an alkyl phosphoramide anionic compound to provide a dialkoxy alkylidene alkyne, and then either (1) hydrolyzing the dialkoxy alkylidene alkyne to form a novel aldehyde, an alkylidene alkynal, and if desired, reducing the triple bond of the alkylidene alkynal to a double bond to obtain the corresponding alkylidene alkenal or (2) first reducing the dialkoxy alkylidene alkyne to form a 1,1-dialkoxy-2-alkylidene-3-alkene and if desired then hydrolyzing said 1,1-dialkoxy-2-alkylidene-3-alkene to form the desired 2-alkylidene-3-alkenal; or (b) firstType: GrantFiled: May 26, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, Alan O. Pittet
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Patent number: 4107066Abstract: Described are hexahydrotetramethyl acetonaphthones and mixtures of such substituted acetonaphthones having the generic formula: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond, and, specifically, the novel isomer having the structure: ##STR2## and processes for the preparation of such mixtures and said novel isomer, as well as a known single component of said mixtures and compounds, by means of first forming 3-chloromesityl oxide from mesityl oxide and chlorine and then reacting the 3-chloromesityl oxide with myrcene via a Diels-Alder reaction thereby producing a chlorine containing Diels-Alder adduct and then either:(i) dehydrochlorinating the chlorine containing Diels-Alder adduct to form an acetyl conjugated cyclohexadiene and cyclizing the acetyl conjugated cyclohexadiene to produce a mixture of isomers having the generic formula: ##STR3## wherein one of the dashed lines is a carbon-carbon double bond and eachType: GrantFiled: July 28, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, James N. Siano, Edward J. Shuster
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Patent number: 4107197Abstract: Described are .alpha.-oxy(oxo) sulfides and ethers having the generic structure: ##STR1## wherein X is one of: ##STR2## Z is one of sulfur or oxygen; when R.sub.1 and R.sub.2 are taken separately, R.sub.1 is hydrogen or methyl, and R.sub.2 is methyl; and when R.sub.1 and R.sub.2 are taken together, R.sub.1 and R.sub.2 form phenyl moieties; and Y is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, acetyl, methoxycarbonylmethyl, or 1,3-diethylacetonyl.Addition of one or more .alpha.Type: GrantFiled: March 31, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Howard H. Heinsohn, Jr.
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Patent number: 4107209Abstract: The compounds 1-[3-(methylthio)butyryl]-2,6,6-trimethyl-cyclohexene and/or the corresponding 1,3-cyclohexadiene analog having the generic structure: ##STR1## wherein the dashed line could be a single or a double carbon-carbon bond and processes and compositions containing same are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma and perfume and perfumed article aroma augmenting and enhancing compositions and for use in foodstuffs, tobacco, perfume and perfumed article aroma imparting compositions; produced by a process illustrated by the reaction: ##STR2## The above-mentioned compounds produce: (A) In food flavorings, sweet, black tea-like, cocoa-like, damascenone-like, chocolate-like, dried fruit-like, rose petal-like aroma characteristics and sweet, black-tea-like, cocoa-like, damascenone-like, chocolate-like, tobacco-like, dried fruit-like and rose petal-like flavor characteristics;(b) In tobacco, a sweet honey-like, rich, slightlyType: GrantFiled: March 3, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, Braja Dulal Mookherjee, Anne Sanderson Hruza, Manfred Hugo Vock, Louis Schmitt Frederick, Joaquin Francisco Vinals
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Patent number: 4107208Abstract: Described are hexahydrotetramethyl acetonaphthones and mixtures of such substituted acetonaphthones having the generic formula: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond.The products produced are useful as vetiver ingredients in perfumes and perfumed articles.Type: GrantFiled: September 19, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, James N. Siano, Edward J. Shuster
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Patent number: 4104203Abstract: Described is a novel perfume material and cologne containing as a key ingredient a mixture of compounds having a sandalwood aroma prepared by a process which comprises:(1) Reacting catechol with camphene in the presence of a Friedel Crafts Catalyst to form a first alkylation product; and then(2) Treating said first alkylation product with hydrogen in the presence of a hydrogenation catalyst, thus forming, initially, diol intermediates and then, on continuing the hydrogenation, the mixture useful in the perfume compositions of our invention.Type: GrantFiled: October 31, 1977Date of Patent: August 1, 1978Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Wilhelmus Johannen Wiegers
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Patent number: 4102928Abstract: Described is a process for preparing a genus of substituted 1-acetyl-3,3-dimethylcyclohexanes having the structure: ##STR1## wherein R.sub.1 or one or both of R.sub.2 and/or R.sub.3 is allyl or methallyl and the other of R.sub.1 or R.sub.2 and/or R.sub.3 is hydrogen, a process for preparing same by means of reacting an allyl or a methallyl halide with acetyl-3,3-dimethyl-cyclohexane using a base according to the reaction: ##STR2## wherein R is allyl or methallyl and wherein X is chloro or bromo.Type: GrantFiled: December 22, 1976Date of Patent: July 25, 1978Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
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Patent number: 4102763Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma and perfume aroma augmenting, enhancing, modifying and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of 1-(3,3-dimethyl-2-norbornyl)-2-propanone (hereinafter referred to as the "norbornylpropanone derivative") having the structure: ##STR1## (which structure is intended to cover both the "endo" and the "exo" isomers thereof).Type: GrantFiled: July 28, 1977Date of Patent: July 25, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, James N. Siano, Manfred Hugo Vock, Edward J. Shuster
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Patent number: 4103036Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma, perfume and perfumed article aroma augmenting, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of one or more derivatives of 1-acetyl-3,3-dimethylcyclohexane having the generic formula: ##STR1## wherein one of the dashed lines may be a carbon-carbon single bond or a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond and R is hydrogen or methyl.Type: GrantFiled: July 28, 1977Date of Patent: July 25, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
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Patent number: 4088696Abstract: Processes for producing novel 2-alkylidene-3-alkynals and 2-alkylidene-3-alkenals which comprise reacting an alkyl metallo acetylide with a dialkoxy acetonitrile or a dialkoxy dialkyl acetamide to form an imine salt, hydrolyzing the imine salt to form a 1,1-dialkoxy-3-alkyn-2-one, alternatively (a) first treating the alkynone with an alkylidene tri-substituted phosphorane or an alkylidene phosphorous triamide or an alkyl phosphoramide anionic compound to provide a dialkoxy alkylidene alkyne, and then either (1) hydrolyzing the dialkoxy alkylidene alkyne to form a novel aldehyde, an alkylidene alkynal, and if desired, reducing the triple bond of the alkylidene alkynal to a double bond to obtain the corresponding alkylidene alkenal or (2) first reducing the dialkoxy alkylidene alkyne to form a 1,1-dialkoxy-2-alkylidene-3-alkene and if desired then hydrolyzing said 1,1-dialkoxy-2-alkylidene-3-alkene to form the desired 2-alkylidene-3-alkenal; or (b) first reducing the alkynone to form a 1,1-dialkoxy-3-alken-2-onType: GrantFiled: April 18, 1977Date of Patent: May 9, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, Alan O. Pittet
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Patent number: 4086927Abstract: Processes and compositions are described for the use in tobacco flavor and aroma augmenting and enhancing compositions and as tobacco aroma and flavor augmenting, imparting and enhancing materials of one or more alkyl side chain methyl unsubstituted 2,2,6-trimethyl-1-cyclohexen-1-vinyl alkanoates (hereinafter referred to as "enol esters") having the generic structure: ##STR1## (which structure is intended to cover both the "cis" and the "trans" isomers thereof) wherein R.sub.1 is straight chain alkyl having 1, 3, 7 or 11 carbon atoms.Type: GrantFiled: September 15, 1976Date of Patent: May 2, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
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Patent number: 4081565Abstract: Processes for imparting a meat flavor to foodstuffs comprising adding thereto a small amount of a processed product of (I) a meat enzymatic digest and, in addition, (II) a sulfur compound such as cysteine or taurine and, if desired, (preferably) (III) thiamine and/or thiazole alkanols and (IV) other free amino acids and/or polypeptides and, in addition, if desired, (V) a monosaccharide and/or a disaccharide, such as sucrose and/or a polysaccharide the product being processed in the absence of any egg (e.g., chicken egg) components; as well as flavoring compositions and flavor enhancing compositions containing such processed products and optional materials and the foodstuffs so obtained.Type: GrantFiled: March 15, 1974Date of Patent: March 28, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Lim Chheang Chhuy, Edgar Allen Day, deceased
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Patent number: 4076852Abstract: Processes for imparting a meat flavor to foodstuffs comprising adding thereto a small amount of a processed product of (I) the whole internal contents of a poultry egg or egg white or egg yolk or enzymatic digest of same, with (II) a poultry meat or other meat powder or enzymatic digest thereof and, in addition, (III) a sulfur compound such as cysteine or taurine and, if desired, (preferably) (IV) thiamine and/or thiazole alkanols and (V) other free amino acids and/or polypeptides and, in addition, if desired, a monosaccharide and/or a disaccharide, such as sucrose and/or a polysaccharide; as well as flavoring compositions and flavor enhancing compositions containing such processed products and optional materials and the foodstuffs so obtained.Type: GrantFiled: March 15, 1974Date of Patent: February 28, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Andries Van Delft, Christopher Giacino
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Patent number: 4069828Abstract: A tobacco article comprising tobacco Tobacco and C.sub.1 -C.sub.6 alkyl-2-methyl-3,4-pentadienoates as a flavor adjuvant.Type: GrantFiled: May 5, 1976Date of Patent: January 24, 1978Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Denis E. Hruza, Manfred Hugo Vock, Joaquin Vinals, Edward J. Shuster
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Patent number: 4049682Abstract: Described are processes for preparing enol esters having the generic structure: ##STR1## (which structure is intended to cover both the "cis" and the "trans" isomers thereof) wherein R.sub.1 is C.sub.1 -C.sub.11 alkyl, and R.sub.4 is hydrogen or methyl, produced by one of the following processes:I. Reacting beta-ionone or a homologue thereof with a peracid;Ii. Reacting an enol acetate formed by process (i) (when R.sub.1 is methyl and R.sub.4 is hydrogen) with an alkanoic acid anhydride or an acyl halide, to form another enol ester;Iii. Reacting beta-cyclohomocitral having the formula: ##STR2## with a lower alkanoic acid anhydride or an acyl halide.Type: GrantFiled: September 15, 1976Date of Patent: September 20, 1977Assignee: International Flavors & Fragrances Inc.Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
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Patent number: 4048201Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma and perfume aroma augmenting, modifying, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product tobacco, perfume and perfumed article aroma imparting materials of one or more alkyl side chain methyl substituted or unsubstituted 2,2,6-trimethyl-1-cyclohexen-1-vinyl alkanoates (hereinafter referred to as "enol esters") having the generic structure: ##STR1## (which structure is intended to cover both the "cis" and the "trans" isomers thereof) wherein R.sub.1 is C.sub.1 -C.sub.11 alkyl and R.sub.4 is hydrogen or methyl.Type: GrantFiled: September 15, 1976Date of Patent: September 13, 1977Assignee: International Flavors & Fragrances Inc.Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
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Patent number: 4045497Abstract: Processes for producing novel 2-alkylidene-3-alkynals and 2-alkylidene-3-alkenals which comprise reacting an alkyl metallo acetylide with a dialkoxy acetonitrile or a dialkoxy dialkyl acetamide to form an imine salt, hydrolyzying the imine salt to form a 1,1-dialkoxy-3-alkyn-2-one, alternatively (a) first treating the alkynone with an alkylidene tri-substituted phosphorane or an alkylidene phosphorous triamide or an alkyl phosphoramide anionic compound to provide a dialkoxy alkylidene alkyne, and then either (1) hydrolyzing the dialkoxy alkylidene alkyne to form a novel aldehyde, an alkylidene alkynal, and if desired, reducing the triple bond of the alkylidene alkynal to a double bond to obtain the corresponding alkylidene alkenal or (2) first reducing the dialkoxy alkylidene alkyne to form a 1,1-dialkoxy-2-alkylidene-3-alkene and if desired then hydrolyzing said 1,1-dialkoxy-2-alkylidene-3-alkene to form the desired 2-alkylidene-3-alkenal; or (b) first reducing the alkynone to form a 1,1-dialkoxy-3-alken-2-oType: GrantFiled: March 8, 1976Date of Patent: August 30, 1977Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, Alan O. Pittet