Patents Represented by Attorney Harold Haidt
  • Patent number: 4108799
    Abstract: 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: Grant
    Filed: July 28, 1977
    Date of Patent: August 22, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, James N. Siano, Edward J. Shuster
  • Patent number: 4107184
    Abstract: 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: Grant
    Filed: October 7, 1975
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr., Manfred Hugo Vock
  • Patent number: 4107093
    Abstract: 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: Grant
    Filed: July 28, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
  • Patent number: 4107217
    Abstract: 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) first
    Type: Grant
    Filed: May 26, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, Alan O. Pittet
  • Patent number: 4107066
    Abstract: 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 each
    Type: Grant
    Filed: July 28, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, James N. Siano, Edward J. Shuster
  • Patent number: 4107197
    Abstract: 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: Grant
    Filed: March 31, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr.
  • Patent number: 4107209
    Abstract: 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, slightly
    Type: Grant
    Filed: March 3, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Wilson, Braja Dulal Mookherjee, Anne Sanderson Hruza, Manfred Hugo Vock, Louis Schmitt Frederick, Joaquin Francisco Vinals
  • Patent number: 4107208
    Abstract: 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: Grant
    Filed: September 19, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, James N. Siano, Edward J. Shuster
  • Patent number: 4104203
    Abstract: 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: Grant
    Filed: October 31, 1977
    Date of Patent: August 1, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Wilhelmus Johannen Wiegers
  • Patent number: 4102928
    Abstract: 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: Grant
    Filed: December 22, 1976
    Date of Patent: July 25, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
  • Patent number: 4102763
    Abstract: 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: Grant
    Filed: July 28, 1977
    Date of Patent: July 25, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, James N. Siano, Manfred Hugo Vock, Edward J. Shuster
  • Patent number: 4103036
    Abstract: 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: Grant
    Filed: July 28, 1977
    Date of Patent: July 25, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
  • Patent number: 4088696
    Abstract: 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-on
    Type: Grant
    Filed: April 18, 1977
    Date of Patent: May 9, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, Alan O. Pittet
  • Patent number: 4086927
    Abstract: 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: Grant
    Filed: September 15, 1976
    Date of Patent: May 2, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
  • Patent number: 4081565
    Abstract: 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: Grant
    Filed: March 15, 1974
    Date of Patent: March 28, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Lim Chheang Chhuy, Edgar Allen Day, deceased
  • Patent number: 4076852
    Abstract: 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: Grant
    Filed: March 15, 1974
    Date of Patent: February 28, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Andries Van Delft, Christopher Giacino
  • Patent number: 4069828
    Abstract: A tobacco article comprising tobacco Tobacco and C.sub.1 -C.sub.6 alkyl-2-methyl-3,4-pentadienoates as a flavor adjuvant.
    Type: Grant
    Filed: May 5, 1976
    Date of Patent: January 24, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Denis E. Hruza, Manfred Hugo Vock, Joaquin Vinals, Edward J. Shuster
  • Patent number: 4049682
    Abstract: 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: Grant
    Filed: September 15, 1976
    Date of Patent: September 20, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
  • Patent number: 4048201
    Abstract: 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: Grant
    Filed: September 15, 1976
    Date of Patent: September 13, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
  • Patent number: 4045497
    Abstract: 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-o
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: August 30, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, Alan O. Pittet