IP Library › Granted Patent US 12,291,689
Granted Patent B2
US 12,291,689 · App. 17/753,502 · Granted May 6, 2025

Compounds for providing a long-lasting floral and fruity odor

Inventors: Andreas Herrmann (Satigny, CH); Alain Trachsel (Satigny, CH)
Assignee: FIRMENICH SA
C11B9/0011C07C317/24C07C323/22C11B9/0034
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Quick Facts
Patent No.
US 12,291,689
App. No.
17/753,502
Granted
May 6, 2025
Kind
B2
Abstract

Described herein are compounds of formula (I) that are able to provide a long-lasting or substantive odor, in particular floral and/or fruity odor, to the environment. Also described herein is a method of imparting a long-lasting odor, in particular a fresh green, floral and/or fruity odor, to surfaces, such as hard surfaces, fabric, skin or hair. Also described herein are a method of using said compounds in perfumery and perfuming compositions or perfumed articles including the compounds described herein.

Claims (45)

1. A compound of formula

wherein

R 1 and R 1′ represent independently from each other a hydrogen atom or a methyl group;

or, both R 1 and/or both R 1′ , when taken together, represent a divalent C 3 to C 8 hydrocarbon group,

R 2 represents a hydrogen atom or C 1 to C 12 hydrocarbon group and R 2′ represents a C 1 to C 12 hydrocarbon group,

R 3 and R 3′ represent independently from each other a hydrogen atom or a C 1 to C 16 hydrocarbon group; or

R 1 and R 3 and/or R 1′ and R 3′ , when taken together, represent a divalent C 2 to C 12 hydrocarbon group,

Q represents a divalent C 4 to C 18 hydrocarbon group, optionally comprising one to eight ether groups and/or one or two functional groups selected from the group consisting of alcohol, ketone, aldehyde, thioether, carboxylic acid, alkali carboxylate, amine, amide, carbamate, nitrile and thiol;

each X represents independently of each other either one of the groups of formulae (i) to (iii)

wherein the wavy line indicates a location of a bond between carbons 2 or 2′ and X and the hatched line indicates a location of a bond between X and Q, provided that the hatched line is not directly linked to a heteroatom or to a carbonyl functional Q; and

wherein the two X groups attached to Q are separated from each other by at least four carbon atoms and provided that 4,4′-(methylenebis(4,1-phenylenesulfonyl))bis(4-methylpentan-2-one) and 4,4′-([1,1′-biphenyl]-4,4′-disulfonyl)bis(4-methylpentan-2-one) are excluded.

2. The compound according to claim 1 , wherein

R 1 and R 1′ represent a hydrogen atom or a methyl group,

R 2 and R 2′ represent a methyl or an ethyl group and

R 3 and R 3′ represent a hydrogen atom or a C 1 to C 10 hydrocarbon group; or R 1 and R 3 and/or R 1′ and R 3′ , when taken together represent a divalent C 2 to C 6 hydrocarbon group,

X represents the groups of formula (i) and/or (ii) and

Q represents a divalent C 4 to C 16 , optionally comprising one to four ether groups and/or with one or two functional groups selected from the group consisting of alcohol, amine and carbamate.

3. The compound according to claim 1 , wherein Q is selected from the group consisting of divalent butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 3-oxapentyl, 3,6-dioxaoctyl, 3,6,9-trioxaundecyl, and 3,6,9, 12-tetraoxatetradecyl.

4. The compound according to claim 1 , wherein the compound of formula (I) is a compound of formula

5. The compound according to claim 1 , wherein the compound of formula (I) is a compound of formula

6. The compound according to claim 1 , wherein the compound of formula (I) is a compound of formula

wherein the dotted lines represent a location of a single or a double bond.

7. The compound according to claim 1 , wherein the compound of formula (I) is a compound of formula

wherein the dotted lines represent a location of a single or a double bond.

8. The compound according to claim 1 , wherein the compound of formula (I) is a compound of formula

9. The compound according to claim 1 , wherein the compound of formula (I) is a compound of formula

10. A method to confer, enhance, improve or modify fresh green, floral and/or fruity odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I) according to claim 1 .

11. A perfuming composition comprising:

i) as perfuming ingredient, at least one compound of formula (I) according to 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, as perfuming ingredient, at least one compound of formula (I) according to claim 1 .

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

14. A method of imparting a long-lasting or substantive fresh green, floral and/or fruity odor to surfaces, the method comprising adding at least one compound of formula (I) according to claim 1 to perfuming compositions or perfumed articles and applying them to a corresponding targeted surface.

15. The perfumed consumer product according to claim 12 , wherein the perfumed consumer product is a fine perfume, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a shampoo, a coloring preparation, a hair spray, a deodorant or antiperspirant, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product, an air freshener, a “ready to use” powdered air freshener, or a hard-surface detergent.

16. A perfumed consumer product comprising the perfuming composition according to claim 11 .

17. The perfumed consumer product according to claim 15 , wherein the perfumed consumer product is a perfume, a fabric care product, a body-care product, an air care product, or a home care product.

18. The perfumed consumer product according to claim 15 , wherein the perfumed consumer product is a fine perfume, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a shampoo, a coloring preparation, a hair spray, a deodorant or antiperspirant, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product, an air freshener, a “ready to use” powdered air freshener, or a hard-surface detergent.

19. The method of claim 14 , wherein the surfaces are hard surfaces, fabric, skin, or hair.

20. The compound according to claim 1 , wherein

R 1 and R 1′ represent a hydrogen atom or a methyl group,

R 2 and R 2′ represent a methyl or an ethyl group and

R 3 and R 3′ represent a hydrogen atom or a C 1 to C 10 hydrocarbon group; or R 1 and R 3 and/or R 1′ and R 3′ , when taken together represent a divalent C 2 to C 6 hydrocarbon group,

X represents groups of formula (i) and/or (ii) and

Q represents a C 4 to C 16 alkyl or alkenyl group, optionally comprising one to four ether groups and/or with one or two functional groups selected from the group consisting of ester, alcohol, amine and carbamate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2022
From: HERRMANN, ANDREAS; TRACHSEL, ALAIN
To: FIRMENICH SA
Reel/Frame 060287/0647 →
Priority Claims (1)
EP 19218158 · Dec 19, 2019 · regional
Continuity (1)
Related Publication 20220340837A1 · Oct 27, 2022
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