Cyclic acetals and ketals and use thereof as fragrance

Patent metadata

Field	Value
Publication number	US-9644171-B2
Application number	US-201414891848-A
Country	US
Kind code	B2
Filing date	Feb 18, 2014
Priority date	May 17, 2013
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

The present invention relates to compounds of the formula (I) and use thereof as fragrance. In a further aspect the present invention relates to compositions and fragrance mixtures containing compounds of the formula (I) and the products perfumed with these compositions and fragrance mixtures.
Further, the present invention relates to a method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette and a method for endowing hair or textile fibers with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette with use of one or more compounds of the formula (I).

First claim

The invention claimed is:

1. A compound of the formula (II) or (II′)

wherein R 1 is hydrogen or C 1 -C 3 alkyl, and R 2 is hydrogen or C 1 -C 4 alkyl, or

(b) according to the formula (III)

wherein R 1 is hydrogen or C 1 -C 3 alkyl, and R 2 hydrogen or C 1 -C 4 alkyl and the compound is saturated or unsaturated, or

(c) according to formula (IV) or (IV′)

wherein R═H or C 1 -C 4 alkyl and R′═H or C 1 -C 3 alkyl.

2. A composition comprising
(i) one or more 3,6,8,8-tetramethyl-octahydro-3a,7-methano-azulen-5,6-diol ketal(s) and
(ii) one or more compound(s) of the formulae (II), (II′), (III), (IV) and/or (IV′) according to claim 1 , wherein
the total content of the compounds of the formulae (II), (II′), (III), (IV) and/or (IV′) is greater than 40 wt. %, based on the total amount of 3,6,8,8-tetramethyl-octahydro-3a,7-methano-azulen-5,6-diol ketal(s) contained in the composition, and/or
wherein
the weight ratio of compound(s) of the formula (IV) to compound(s) of the formula (IV′), if present, lies in the range from 4:1 to 1:10.

3. A fragrance mixture, comprising a composition according to claim 2 , as well as one or more (further) compound(s) not corresponding to the fragrances of the formulae (II), (III), (IV), or (IV′), wherein
(i) the quantity of the compound(s) of the formulae (II), (II′), (III), (IV), or (IV′), is sufficient to mediate an ambergris and/or wood fragrance note, and/or
(ii) the (further) fragrances not corresponding to the formulae (II), (II′), (III), (IV), or (IV′), mediate one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette and the quantity of the compound(s) of the formula (II), (II′), (III), (IV), or (IV′), is sufficient to modify and/or to intensify one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette, and/or
(iii) the quantity of the compound(s) of the formulae (II), (II′), (III), (IV), or (IV′), is sufficient to impart to the fragrance mixture an impression of volume, complexity, elegance and/or naturalness, and/or
(iv) the quantity of the compound(s) of the formulae (II), (II′), (III), (IV), or (IV′), is sufficient, in comparison to an otherwise identically constituted fragrance mixture without compounds of the formulae (II), (II′), (III), (IV), or (IV′), to create a more nurturing, more harmonious, higher quality and/or more natural olfactory impression.

4. A method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following step:
(i) providing one or more fragrance(s) with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, and
(ii) mixing said one or more fragrance(s) with
(ii-ii) the composition according to claim 2 in a quantity which suffices to intensify the olfactory impression of the fragrance(s).

5. A perfumed product containing a composition, according to claim 2 , in a sensorily effective quantity, wherein the product contains one or more surfactants.

6. A method for intensifying an odor, comprising incorporating a compound as claimed in claim 1 into a
fragrance or fragrance mixture,
means for increasing substantivity and/or retention of a fragrance mixture, or fixative.

7. A fragrance mixture, comprising
one or more compound(s) of the formulae (II), (II′), (III), (IV) and/or (IV′) according to claim 1 , as well as
one or more (further) compound(s) not corresponding to the fragrances of the formulae (II), (II′), (III), (IV) or (IV′), wherein

(i) the quantity of the compound(s) of the formulae (II), (II′), (III), (IV) or (IV′), is sufficient to mediate an ambergris and/or wood fragrance note, and/or
(ii) the (further) fragrances not corresponding to the formulae (II), (II′), (III), (IV), or (IV′), mediate one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette and the quantity of the compound(s) of the formula (II), (II′), (III), (IV), or (IV′), is sufficient to modify and/or to intensify one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette, and/or
(iii) the quantity of the compound(s) of the formulae (II), (II′), (III), (IV), or (IV′), is sufficient to impart to the fragrance mixture an impression of volume, complexity, elegance and/or naturalness, and/or
(iv) the quantity of the compound(s) of the formulae (II), (II′), (III), (IV), or (IV′), is sufficient, in comparison to an otherwise identically constituted fragrance mixture without compounds of the formulae (II), (II′), (III), (IV), or (IV′), to create a more nurturing, more harmonious, higher quality and/or more natural olfactory impression.

8. The fragrance mixture, of claim 7 , wherein the quantity of the compound(s) of the formulae (II), (II′), (III), (IV), or (IV′), lies in the range from 0.0001 to 25 wt. %, based on the total weight of the fragrance mixture.

9. The fragrance mixture of claim 7 , further containing
(i) one or more wood and/or ambergris fragrance(s) not corresponding to the formulae (II), (II′), (III), (IV), or (IV′), and/or
(ii) one or more musk fragrance(s).

10. The fragrance mixture of claim 9 , wherein the musk fragrance(s) is/are selected from the group consisting of macrocyclic musk fragrances, nitro musk fragrances, polycyclic musk fragrances, alicyclic musk fragrances and mixtures thereof.

11. The fragrance mixture of claim 9 , wherein the weight ratio of musk fragrances to the compound(s) of the formulae (II), (II′), (III), (IV) or (IV′), lies in the range from 100:1 to 100,000:1.

12. A method for endowing hair or textile fibers with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following steps:
(i) preparing a fragrance mixture according to claim 7 , wherein the (further) fragrance(s) not corresponding to the formulae (II), (II′), (III), (IV), or (IV′), mediate(s) one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette and the quantity of the compound(s) of the formulae (II), (II′), (III), (IV), or (IV′), is sufficient to modify and/or to intensify one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette, and
(ii) applying the fragrance mixture onto the hair or the textile fibers.

13. A method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following step:
(i) providing one or more fragrance(s) with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, and
(ii) mixing said one or more fragrance(s) with
(ii-iii) the fragrance mixture of claim 7 in a quantity which suffices to intensify the olfactory impression of the fragrance(s).

14. A perfumed product containing a fragrance mixture, according to claim 7 , in a sensorily effective quantity, wherein the product contains one or more surfactants.

15. A method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following step:
(i) providing one or more fragrance(s) with one, several or all of the notes selec

Assignees

• Symrise Ag

Inventors

• Hölscher Bernd

Classifications

• C11B9/0088

  Spiro compounds · CPC title

• A61K8/498

  having 6-membered rings or their condensed derivatives, e.g. coumarin · CPC title

• D06M13/005

  Compositions containing perfumes; Compositions containing deodorants · CPC title

• C07D317/70

  condensed with ring systems containing two or more relevant rings · CPC title

• A61K8/4973

  with oxygen as the only hetero atom · CPC title