International Flavors & Fragrances Inc.

Augustinus G Van Loveren

Richard M Boden

Frederick L Schmitt

Lambert Dekker

Marie R Hanna

Manfred H Vock

Wilhelmus J Wiegers

Domenick Luccarelli, Jr

David R Bowen

Braja D Mookherjee

William J Evers

Anton Van Ouwerkerk

Mark A Sprecker

Marina A Munteanu

Geoffrey B Seaber

Robert P Belko

Patrick Whelan

John B Hall

Described is an article which dispenses at a constant rate a volatile composition of matter into the atmosphere surrounding the article which volatile composition of matter can be, for example, a perfume composition or air freshener, which article is a container which is a hollow totally enclosed flexible, rigid or partially flexible-partially rigid structure comprising a thin shell totally enclosing an inner void, with the thin shell having a part thereof as a microporous polymer which contains a plurality of finite filler particles which that when the article is located in the ambient environment, the volatile material molecules are passed through the microporous polymer by means of an adsorption desorption mechanism or by means of capillary action. The volatile substance which is a composition of matter is enabled to pass through the microporous polymer at a constant mass flow rate of both the individual volatile components and the total composition. Thus, the composition of matter passing through the microporous polymer remains unchanged insofar as its composition is concerned. The invention is enabled using a microporous polymer having the property of transporting water vapor at a rate of between 100 up to a 1000 g/m.sup.2 /day at about 25.degree. C. and at about 50% relative humidity at about atmospheric pressure and having an air transport rate of 100-20,000 Gurley seconds (gs) and a thickness in the range of from about 0.01 mils up to about 20 mils.

Article which dispenses at a constant rate a volatile composition, and

Described is an article useful for dispensing at a constant rate, continuously or discontinuously for discrete periods of time a volatile composition of matter such as an air freshener or perfume composition into the atmosphere surrounding said article, the article being a hollow totally enclosed flexible, rigid or partially flexible-partially rigid structure comprising a thin shell totally enclosing an inner void with part of the thin shell comprising a microporous polymer containing a plurality of finite solid filler particles whereby when the article is located in the ambient environment, the volatile material molecules are transported through the porous polymer at a substantially constant mass flow rate both of the individual volatile components and totally through the porous polymer. The functioning of the article is enabled because the microporous polymer section has (i) the property of transporting water vapor at a rate of between 50 up to 1000 g/m.sup.2 /day at about 25.degree. C. and at about 50% relative humidity at about atmospheric pressure and having an air transport rate of 100-20,000 Gurley seconds and a thickness in the range of from about 0.01 mils up to about 20 mils.

Constant rate volatile composition dispensing article and process for

Described is 2-n-pentyl-2-cyclohexen-1-one having the structure: ##STR1## useful in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes, and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles as well as hair sprays, shampoos, bath oils and perfumed polymers.

Perfumery uses of 2-n-pentyl-2-cyclohexen-1-one

Described is a process for producing 1,1,4,7-tetramethyl-3-indanone defined according to the structure: ##STR1## the 1,1,4,7-tetramethyl-3-indanone per se and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.

1,1,4,7-Tetramethyl-3-indanone, product produced thereby and

Described for use in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes and perfumed articles, foodstuffs, chewing gums, toothpastes and medicinal products are the cis and/or trans isomers of the macrocyclic lactone defined according to the structure: ##STR1## produced according to the process of first reacting the ester defined according to the structure: ##STR2## with the alkenol having the structure: ##STR3## in order to produce the di-unsaturated ester having the structure: ##STR4## and then causing the said diester to undergo an internal metathesis to form the compound having the structure: ##STR5##

Use of macrocyclic lactone in augmenting or enhancing aroma or taste of

Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## in order to produce the ketone defined according to the structure: ##STR4## which is hydrogenated to form the compound having the structure: ##STR5## and further hydrogenated to form the ketone having the structure: ##STR6## This ketone is reacted with CH.sub.3 M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: ##STR7## These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: ##STR8##

1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for

Described are 1-oxoalkyl-2-isopropylnorbornane derivatives defined according to the generic structure: ##STR1## wherein X represents a moiety selected from the group consisting of: ##STR2## wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond and wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that R.sub.1 and R.sub.2 are not both methyl, and uses thereof in augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, colognes and perfumed articles. Also described are processes for preparing said 1-oxoalkyl-2-isopropylnorbornane derivatives by means of a low temperature catalytic Diels Alder reaction or high temperature thermal Diels Alder reaction between a bicyclopentadiene derivative and 2-methyl-3- buten-5-one according to the reaction: ##STR3## wherein R represents methyl or hydrogen.

1-Oxoalkyl-2-isopropylnorbornane derivatives, uses thereof in augmenting

Described is a class of macrocyclic carbonates defined according to the structure: ##STR1## wherein n is an integer of from 1 up to 8 and m is an integer of from 1 up to 8 and where n and m may be the same or different and organoleptic use thereof in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, colognes and perfumed articles (i.e. solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and perfumed polymers).

Perfuming with a macrocyclic carbonate

Described is a novel process for preparing 1,2,3,3,5,6-hexamethyl- bicyclo [2,2,2.] oct-5-en-2-ol by using 2,6,6-trimethylcyclohexa-2,4-diene-1-one as a starting material.

Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same. Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.1 is oxymagnesium halide and R.sub.2 is methyl; and wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl with the provisos that:

Methyl substituted-2-oxohexane derivatives and processes for preparing

Described is a process for producing 1,1-dimethyl-3-indanones defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represents hydrogen or methyl with the proviso that at least one of R.sub.1 and R.sub.2 methyl, products produced thereby and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.

Process for producing 1,1-dimethyl-3-indanones, products produced

Described is a class of macrocyclic carbonates defined according to the structure: ##STR1## wherein n is an integer of from 1 up to 8 and m is an integer of from 1 up to 8 and where n and m may be the same or different and organoleptic uses thereof in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, colognes and perfumed articles (i.e. solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and perfumed polymers).

Flavoring with a macrocyclic carbonate

Described are isopropyl substituted cyclohexenyl methyl ketones defined according to the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.11 and R.sub.21 each represents hydrogen or methyl with the provisos that:

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Rye, NY, United States of America

Augustinus G Van Loveren