Enol ether properfume

Patent metadata

Field	Value
Publication number	US-2025049660-A1
Application number	US-202218719325-A
Country	US
Kind code	A1
Filing date	Dec 14, 2022
Priority date	Dec 14, 2021
Publication date	Feb 13, 2025
Grant date	—

Abstract

The present invention relates to enol ether compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method to release a compound being an aldehyde compound of formula (II), a formate ester of formula (III) and/or an alcohol of formula (IV), by exposing the enol ether compound of formula (I) to an environment wherein it is oxidized. Moreover, the present invention relates to a perfuming composition and a perfumed consumer product comprising at least one enol ether compound of formula (I).

First claim

1 . A method to release from a precursor compound, compounds selected from the group consisting of
a) an aldehyde compound of formula

wherein
R 1 is a C 1-15 alkyl, C 3-15 alkenyl, C 3-15 cycloalkyl, C 5-15 cycloalkenyl or C 3-14 heterocycloalkyl group, each optionally substituted with one or more of a hydroxy, C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 2-15 alkenyloxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 3-15 heterocycloalkyl, carboxylic acid, C 1-4 carboxylic ester, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy, carboxylic acid and/or C 1-4 carboxylic ester group;
b) a formate ester of formula

R 2 is a C 4-18 hydrocarbon group optionally comprising one or two oxygen atoms; provided that an ester functional group alpha to the formyloxy group is excluded and provided that R 2 does not comprise an allylic functional group;
c) an alcohol of formula

wherein R 2 has the same meaning as defined above;
wherein the precursor compound comprises a compound of formula (I)

in the form of any one of its stereoisomers or a mixture thereof, and wherein R 1 and R 2 have the same meaning as defined above;
by exposing the precursor compound of formula (I) to an environment wherein the compound is oxidized.

2 . The method according to claim 1 , wherein the compound of formula (I) is a C 18 -C 36 compound.

3 . The method according to claim 1 , wherein R 2 is a C 5-18 hydrocarbon group optionally comprising one or two oxygen atoms.

4 . The method according to claim 1 , wherein R 2 is a C 6-18 hydrocarbon group optionally comprising one or two oxygen atoms.

5 . The method according to claim 1 , wherein R 2 is a C 1-15 alkyl, C 2-15 alkenyl, C 3-15 cycloalkyl or C 5-15 cycloalkenyl group, each optionally substituted with one or more of a hydroxy, C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy and/or carboxylic acid.

6 . The method according to claim 1 , wherein R 1 is a C 1-10 alkyl, C 3-10 alkenyl, C 3-11 cycloalkyl or C 5-11 cycloalkenyl group, each optionally substituted with one or more of a hydroxy, C 1-4 alkyl, C 1-4 alkoxy, C 3-8 cycloalkyl, C 5-8 cycloalkenyl, C 6 aryl and/or C 6 aryloxy group, each optionally substituted with one or more of a C 1-4 alkyl, hydroxy and/or C 1-4 alkoxy group.

7 . The method according to claim 1 , wherein the compound of formula (II), (III) and/or (IV) are a perfuming ingredient.

8 . The method according to claim 1 , wherein the environment wherein the compound is oxidized is air.

9 . A method to confer, enhance, improve or modify the odor properties of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, comprising adding to the composition, the air, or article, or contacting or treating the surface with an effective amount of at least one compound of formula (I) as defined in claim 1 .

10 . A method for intensifying or prolonging the diffusion effect of the characteristic fragrance of at least one aldehyde compound of formula (II), of at least one active formate ester of formula (III) and/or of at least one active alcohol of formula (IV) as defined in claim 1 , on a surface or the air surrounding the perfuming composition, wherein the surface, or the air is treated with at least one compound (I) as defined in claim 1 , or with a composition or article containing at least one compound (I), under conditions susceptible of allowing the release of at least one ketone or aldehyde formula (II), of at least one formate ester of formula (III) and/or of at least one alcohol of formula (IV) over time.

11 . A perfuming composition comprising
i) at least one compound of formula (I), as defined in claim 1 ; ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and iii) optionally at least one perfumery adjuvant.

12 . A perfumed consumer product comprising at least one compound of formula (I), as defined in claim 1 .

13 . The perfumed consumer product according to claim 12 , wherein the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.

14 . The perfumed consumer product according to claim 13 , wherein the perfumery consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent optionally in the form of a pod or tablet, a fabric softener, a liquid or solid scent booster, a dryer sheet, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a leave-on or rinse-off hair conditioner, a coloring preparation, a color-care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, skin cream or lotion, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun or after sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, oil or gel, a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard-surface detergent, a leather care product, a car care product.

15 . A compound of formula

in the form of any one of its stereoisomers or a mixture thereof and wherein
R 1 comprises at least 6 carbon atoms and is a C 1-15 alkyl, C 3-15 alkenyl, C 3-15 cycloalkyl, C 5-15 cycloalkenyl or C 3-14 heterocycloalkyl group, each optionally substituted with one or more of a hydroxy, C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 2-15 alkenyloxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 3-15 heterocycloalkyl, carboxylic acid, C 1-4 carboxylic ester, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy, carboxylic acid and/or C 1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom, provided that R 1 is not a 2-hexylidenecyclopentyl group;
R 2 is a C 6-18 hydrocarbon group optionally comprising one or two oxygen atoms, provided that an ester functional group alpha to the oxy group is excluded; and
provided that R 2 is not a benzyl group or a cyclohexyl group or 2-hydroxy-1,2-diphenylethyl, or a 1-(tert-butoxy)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl group and does not comprise an allylic functional group; and provided that 1-(heptyloxy)dec-1-ene, 1-(decyloxy)dec-1-ene, 1-(dodecyloxy)dodec-1-ene, (4-phenethoxybut-3-en-1-yl)benzene and 1-((3,7-dimethyloctyl)oxy)-3,7-dimethyloct-1-ene are excluded.

16 . The method according to claim 2 , wherein the compound of formula (I) is a C 20-36 compound.

Assignees

• Firmenich & Cie

Inventors

• Womack Gary Bernard

Classifications

• C07C43/16

  Vinyl ethers · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• A61K2800/57

  Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances · CPC title

• A61K8/33 Primary

  containing oxygen · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title