Patents Represented by Attorney Harold Haidt
  • Patent number: 4000090
    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 2,2,6-trimethyl-1-cyclohexen-1-ylacetaldehyde enol esters (hereinafter referred to as "beta-cyclohomocitral 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.5 lower alkyl.Addition of the one or more beta-cyclohomocitral enol esters to consumable materials is indicated to produce:A.
    Type: Grant
    Filed: October 7, 1975
    Date of Patent: December 28, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
  • Patent number: 3998873
    Abstract: A process for producing one or more alkyl-2-methyl pentenoates having the generic structure: ##STR1## comprising the steps of: I. Contacting with hydrogen gas one or more alkyl-2-methyl-3,4-pentadienoates having the structure: ##STR2## in the presence of a hydrogenation catalyst which may be either of: A. Raney Nickel;B. Palladium on carbon; orC. Palladium on calcium carbonateAt a temperature from about 10.degree. C up to about 100.degree. C, a hydrogen pressure from about 5 psig up to about 80 psig, the concentration of said catalyst based on the weight of the starting material, the alkyl-2-methyl-3,4-pentadienoate, being from about 0.1% up to about 10%;Ii. Recovering at least 60% by weight of one or more alkyl-2-methyl-cis-3-pentenoates having the structure: ##STR3## wherein R is alkyl having up to 6 carbon atoms; optionally III. Separating the ingredients of the resulting chemical composition to obtain ethyl-2-methyl-cis-3-pentenoate; and/or, optionally,Iv.
    Type: Grant
    Filed: April 21, 1975
    Date of Patent: December 21, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Denis E. Hruza
  • Patent number: 3996250
    Abstract: 3-Furyl beta-chalcogencycloaklyl sulfides having the structure: ##STR1## wherein X is a chalcogen selected from the group consisting of oxygen and sulfur; and R.sub.2 and R.sub.3 are each selected from the group consisting of methyl and hydrogen, at least one of R.sub.2 or R.sub.3 being methyl, the moieties X and S being in a trans relationship, such 3-furyl beta-chalcogencycloalkyl sulfides being useful in altering, modifying or enhancing the organoleptic properties of foodstuffs.
    Type: Grant
    Filed: September 17, 1975
    Date of Patent: December 7, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Igor A. Pelse, Manfred Hugo Vock
  • Patent number: 3996169
    Abstract: Processes and compositions for altering, modifying, enhancing (or imparting) the aroma of (or to) consumable products including colognes, perfumes and perfumed articles using as the essential ingredient at least one organic tricyclic alcohol having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 is selected from the group consisting of hydrogen and methyl; wherein the dashed line is carbon-carbon single bond or a carbon-carbon double bond; wherein R.sub.1 is limited to hydrogen when (i) the dashed line is a carbon-carbon single bond; (ii) R.sub.2, R.sub.3, R.sub.4, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 is hydrogen and (iii) R.sub.5 is hydrogen or methyl and wherein when the dashed line is a carbon-carbon single bond, one of R.sub.3 or R.sub.4 is hydrogen.
    Type: Grant
    Filed: September 17, 1975
    Date of Patent: December 7, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Edward J. Shuster, Joaquin F. Vinals, Manfred Hugo Vock
  • Patent number: 3996287
    Abstract: Process for producing 2-mercapto alkane-1,4-diones comprising the steps of:I. Providing a 2-ene-1,4-dione having the structure: ##STR1##ii. Intimately admixing said 2-ene-1,4-dione with a sulfur compound having the formula:R.sub.3 SHthereby providing a substituted or unsubstituted 2-thia substituted alkane 1,4 dione having the structure: ##STR2##iii. Hydrolyzing said 2-thia substituted 1,4 dione thereby forming a 2-mercapto alkane-1,4-dione having the structure: ##STR3## wherein R.sub.3 is selected from the group consisting of acyl and aroyl, wherein R.sub.2 is lower alkyl; and wherein R.sub.4 and R.sub.6 are the same or different and are selected from the group consisting of hydrogen and lower alkyl; wherein when R.sub.1 is hydrogen, the reaction (ii) is carried out in the presence of an organic base; and wherein when R.sub.1 is lower alkyl, the reaction (ii) is carried out in the absence of catalyst or in the presence of catalyst.
    Type: Grant
    Filed: July 8, 1975
    Date of Patent: December 7, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr., Bernard J. Mayers
  • Patent number: 3996170
    Abstract: Perfume and fragrance compositions, and perfumed articles comprising one or more 6-alkyl-alpha-pyrones having the generic structure: ##STR1## wherein R.sub.1 is methyl or hydrogen and R.sub.2 is C.sub.3 -C.sub.5 alkyl, and processes for preparing same are described.
    Type: Grant
    Filed: September 17, 1975
    Date of Patent: December 7, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Edward J. Shuster, Alan Owen Pittet
  • Patent number: 3996296
    Abstract: Described are the novel compounds, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanol and 4-(6,6-dimethyl-2-methylene-3-cyclohexen-1-yl)-2-butanol, and processes for preparing the aforementioned alcohols and acetate esters thereof.
    Type: Grant
    Filed: March 24, 1975
    Date of Patent: December 7, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja Dulal Mookherjee, Manfred Hugo Vock, Carlos Benaim, Edward J. Shuster
  • Patent number: 3991123
    Abstract: Described is a genus of novel compounds, defined by the generic structure: ##SPC1##Wherein n is 0 or 1 and X is selected from the group consisting of 1,2-cyclo-propylene having the structure: ##SPC2##And 1,2-ethenylene having the structure: ##SPC3##X being cyclopropylene when n is 1, useful for altering, enhancing, modifying or imparting an aroma of or to consumable products including perfumes, perfume comositions and perfumed articles.
    Type: Grant
    Filed: September 17, 1975
    Date of Patent: November 9, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja Dulal Mookherjee, Robert Walter Trenkle, Kenneth K. Light, Edward J. Shuster
  • Patent number: 3991214
    Abstract: Methods for preparing tobaccos, medicinal products, chewing gums, foodstuffs and flavoring compositions for tobaccos, chewing gums, foodstuffs and medicinal products by including therein 2-phenyl-3-carboethoxyfuran to produceA. In chewing gum, medicinal product and foodstuff flavorings, concord grape, wine, pungent, weak sweet buttery, sweet carrot, dry woody cinnamon or warm benzaldehydenut like flavor notes or combinations of these and bitter after taste, benzoateester taste and heavy floral backnotes for improving the taste and aroma of artificial grape or other fruit flavoring compositions;B. In tobacco flavorings, aromatic, sweet, resinous and balsamic-like notes as well as the foodstuff flavoring compositions, perfume compositions and tobacco compositions containing 2-phenyl-3-carboethoxyfuran.
    Type: Grant
    Filed: August 12, 1975
    Date of Patent: November 9, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Gary Slangan, Alan O. Pittet, Christopher Giacino, Denis E. Hruza, Sr., Edward J. Shuster
  • Patent number: 3989760
    Abstract: Processes and compositions for altering the flavor and/or aroma of consumable products including foods, tobacco and perfumes utilizing as the essential ingredient the novel organic tricyclic alcohol having the formula: ##SPC1##And a process for preparing the above-mentioned compounds involving first intimately admixing a tetramethyl cyclohexadienone having the structure: ##SPC2##With 3-butenyl lithium having the structure: ##SPC3##Thereby forming a triene compound having the structure: ##SPC4##And then heating the triene compound at an elevated temperature and pressure thereby producing a metallo tricyclic compound having the structure: ##SPC5##Which is then hydrolyzed to form the tricyclic alcohol of this invention having the structure: ##SPC6##
    Type: Grant
    Filed: November 20, 1975
    Date of Patent: November 2, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Edward J. Shuster, Joaquin F. Vinals, Manfred Hugo Vock
  • Patent number: 3989856
    Abstract: 3-Furyl beta-oxoalkyl sulfides having the structure: ##SPC1##Wherein R.sub.4 is C.sub.3 alkyl and R.sub.5 is C.sub.4 alkyl with R.sub.4 being 2-propyl when R.sub.5 is 2-methyl-1-propyl; and R.sub.4 being 1-propyl when R.sub.5 is 1-butyl, such 3-furyl beta-oxoalkyl sulfides taken alone or in admixture being useful in altering or modifying or enhancing the organoleptic properties of foodstuffs, foodstuffs containing same, and foodstuff flavoring compositions containing such 3-furyl beta-oxoalkyl sulfides.
    Type: Grant
    Filed: November 20, 1975
    Date of Patent: November 2, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr., Christopher Giacino
  • Patent number: 3988510
    Abstract: Novel 3-furyl sulfides having the formula: ##SPC1##Wherein R.sub.1 is selected from the group consisting of aralkyl, nitrogenheterocyclic, alkenyl and alkylthioalkyl; and 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, such 3-furyl sulfides being useful in modifying or enhancing the organoleptic properties of foodstuffs (e.g. taste and/or aroma).
    Type: Grant
    Filed: May 29, 1975
    Date of Patent: October 26, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr., Manfred Hugo Vock, Christopher Giacino
  • Patent number: 3987803
    Abstract: Described is a process comprising adding to tobacco (for subsequent incorporation into smoking articles along with tobacco blend) an amount sufficient to alter the flavor or aroma of the tobacco of 2-methyl-4-pentenoic acid and/or ethyl-2-methyl-4-pentenoate.
    Type: Grant
    Filed: April 21, 1975
    Date of Patent: October 26, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Ching Y. Tseng, Manfred Hugo Vock, Joaquin Vinals, Edward J. Shuster
  • Patent number: 3988487
    Abstract: Methods for altering, modifying or enhancing the organoleptic properties of foodstuffs and perfumes comprising incorporating with such materials a small but effective amount (from 0.02 ppm up to about 150 ppm) of at least one 2-alkylidene-cis-3-alkenal or at least one 2-alkylidene-trans-3-alkenal or a mixture having at last one 2-alkylidene-trans-3-alkenal and one 2-alkylidene-cis-3-alkenal represented by the formula: ##SPC1##Or di-lower alkyl acetal thereof wherein one of R.sub.1 and R.sub.2 is hydrogen and the other is lower alkyl; and one of R.sub.3 and R.sub.4 is hydrogen and the other is lower alkyl; together with compositions containing the said 2-alkylidene-3-alkenals or acetals thereof for use in altering such organoleptic properties.
    Type: Grant
    Filed: August 12, 1975
    Date of Patent: October 26, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anne Sanderson, Gerard Mosciano, Alan O. Pittet, Louis J. Strasburger, William L. Schreiber, Michel Van Praag, Edward J. Shuster, Bernard J. Rutkowsky, William J. Evers
  • Patent number: 3985908
    Abstract: Novel 3-furyl sulfides having the formula: ##SPC1##Wherein R.sub.2 and R.sub.2 are each selected from the group consisting of hydrogen and methyl; at least one of R.sub.2 and R.sub.3 being methyl, such 3-furyl sulfides being useful in modifying or enhancing the organoleptic properties of foodstuffs (e.g. taste and/or aroma).
    Type: Grant
    Filed: March 12, 1976
    Date of Patent: October 12, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr., Manfred Hugo Vock, Christopher Giacino
  • Patent number: 3985907
    Abstract: 3-Furyl beta-chalcogenalkyl sulfides having the structure: ##SPC1##Wherein n is 1 or 2; R.sub.2 and R.sub.3 are each selected from the group consisting of methyl and hydrogen, at least one of R.sub.2 and R.sub.3 being methyl; and R.sub.4 and R.sub.5 taken separately, are each lower alkyl, or R.sub.4 and R.sub.5 taken together complete a cycloalkyl or bicycloalkyl group, such 3-furyl beta-oxoalkyl sulfides taken alone or in admixture being useful in altering or modifying or enhancing the organoleptic properties of foodstuffs, and processes for preparing these 3-furyl beta-oxalkyl sulfides where n is 1 using the reaction: ##SPC2##Wherein X is halogen selected from the group consisting of chlorine and bromine; wherein M is alkali metal and R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each defined as above.
    Type: Grant
    Filed: May 29, 1975
    Date of Patent: October 12, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr., Manfred Hugo Vock, Christopher Giacino
  • Patent number: 3984579
    Abstract: Methods are described for producing mixtures containing greater than 50% 2-methyl-cis-3-pentenoic acid as well as substantially pure 2-methyl-cis-3-pentenoic acid for preparing foodstuffs, flavoring compositions for foodstuffs, chewing gum compositions, flavoring compositions for chewing gum, medicinal product compositions and ingredients for medicinal product compositions by including therein the isomeric mixtures containing greater than 50% cis-2-methyl-3-pentenoic acid produced by the above-stated processes in order to produce in foodstuff flavorings, medicinal product flavorings and chewing gum flavorings, a sweet, fruity, strawberry, winey-cognac, butter-like, rum-like and butterscotch aroma and a sweet, strawberry, nutty-coconut, fatty, butter-like, rum-like and butterscotch-like taste with fruity, coconut-like isovaleric undertones.
    Type: Grant
    Filed: May 9, 1975
    Date of Patent: October 5, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Manfred Hugo Vock, Joaquin Vinals, Edward J. Shuster
  • Patent number: 3982038
    Abstract: 3-Furyl .beta.-chalcogenalkyl sulfides having the structure: ##SPC1##Wherein X is a chalcogen selected from the group consisting of oxygen and sulfur; R.sub.2 and R.sub.3 are each selected from the group consisting of methyl and hydrogen, at least one of R.sub.2 and R.sub.3 being methyl; and R.sub.4 and R.sub.5, taken separately, are each methyl, or R.sub.4 and R.sub.5 taken together are tetramethylene, and when R.sub.4 and R.sub.5 taken together are tetramethylene X and S are in a trans relationship, are indicated to be useful in altering, modifying or enhancing the taste and/or aroma of foodstuffs.
    Type: Grant
    Filed: September 17, 1975
    Date of Patent: September 21, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Igor A. Pelse, Manfred Hugo Vock
  • Patent number: 3982034
    Abstract: A small but effective amount of a compound represented by the formula ##SPC1##Wherein R.sub.1, R.sub.3, and R.sub.5 are the same and are lower alkyl of from 1 to 5 carbon atoms and R.sub.2, R.sub.4, and R.sub.6 are the same and are hydrogen or lower alkyl of from 1 to 5 carbon atoms, is used to alter the flavor and aroma characteristics of a consumable material.
    Type: Grant
    Filed: March 21, 1975
    Date of Patent: September 21, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard Arnold Wilson, Ira Katz, Manfred H. Vock, Edward J. Shuster
  • Patent number: 3981924
    Abstract: A superatmospheric process for directly producing a Diels-Alder adduct which comprises admixing:I. A conjugated diene which can be either alpha-terpinene, allo-ocimene, cyclopentadiene or myrcene; withIi. A carbonyl group-containing compound which can be either acetone, acetaldehyde propionaldehyde or methylethyl ketone; withIii. An aldehyde source which can be either a formaldehyde source or an acetaldehyde source which aldehyde source will yield formaldehyde or acetaldehyde; in the presence ofIv. A secondary amine catalyst such as a lower dialkyl amine or a cyclic amine such as morpholine, pyrrolidine or piperidine,At a temperature in the range of from about 120.degree. up to about 200.degree.C for a period of time from about 2 hours up to about 8 hours, and novel products produced therefrom to wit:I. A mixture of compounds having the structures: ##SPC1##Ii. A mixture of compounds having the structure: ##SPC2##andIii.
    Type: Grant
    Filed: June 26, 1975
    Date of Patent: September 21, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventor: John B. Hall