EP0200890B1 - Use of a spirolactone as a perfuming agent - Google Patents

Description

The present invention relates to the field of perfumery. It relates in particular to the use of a spirannic lactone of formula (I) or 1-oxaspiro [4.5] decan-2-one, as a perfuming agent.

The subject of the invention is also a perfuming composition characterized in that it contains, as active perfuming agent, said spirannic lactone.

The invention is defined as indicated in the claims.

• - G. I. Nikishin et V. D. Vorob'ev, Isvestiya Akade- mü Nauk SSSR, Otdelenie Khimicheskikh Nauk 10 (1962) 1874-76 ;
• - P. Canonne et al., J. Org. Chem., 46, 3091-7 (1981);
• - S. Tatsuya et al., Tetrahedron Lett. 21, 5029-32 (1980) ;
• - R. M. Jacobson et J. W. Clader, Tetrahedron Lett. 21, 1205-8 (1980) ;
• - P. Canonne et al., J. Org. Chem. 45, 1828-35 (1980).

To date, numerous reports have appeared in the scientific literature dealing with the synthesis of spirannic lactones. We can refer in this regard to the articles published by J. Moulines and R. Lande in Accounts Rend. 261, 1983 (1965) and in Bull. Soc. Chim. France 1075-80 (1971), or to one of the following publications:

• - GI Nikishin and VD Vorob'ev, Isvestiya Akademü Nauk SSSR, Otdelenie Khimicheskikh Nauk 10 (1962) 1874-76;
• - P. Canonne et al., J. Org. Chem., 46, 3091-7 (1981);
• - S. Tatsuya et al., Tetrahedron Lett. 21, 5029-32 (1980);
• - RM Jacobson and JW Clader, Tetrahedron Lett. 21, 1205-8 (1980);
• - P. Canonne et al., J. Org. Chem. 45, 1828-35 (1980).

Japanese patent application, published under No. 55/76843 on June 10, 1980, describes a process for the preparation of cycloaliphatic esters from spirannic lactone (I). This application does not however mention the useful odorous properties of the lactone in question.

European patent application, published under the number 105157 on April 11, 1984, describes a series of spiran lactones of formula (II) in which R denotes an alkyl residue d-4, as well as their use in perfumery. This European application makes no mention or suggestion as to the possible use of the 1-oxaspiro [4.5] decan-2-one of the invention.

The table below describes the compounds defined using the formula (II), as well as their odorous characteristics as given in the cited European application.

As preferred compounds are 8-isopropyl-1-oxaspiro [4.5] decan-2-one and 8-ethyl-1-oxaspiro [4.5] decan-2-one.

We have now unexpectedly found that 1-oxaspiro [4.5] decan-2-one also has interesting odorous properties and that, therefore, it could be used as an active perfuming ingredient for the preparation of perfumes and perfuming bases and for the perfuming of various articles such as soaps, detergents, solid and liquid, ionic, anionic, zwitterionic or non-ionic, textile softeners, cleaning products or cosmetics, shampoos and body deodorants. Used as active adjuvant in polymeric bases or various resins, the lactone of the invention can serve as active principle for deodorizing or sanitizing devices for ambient air or closed chambers.

The smell of 1-oxaspiro [4.5] decan-2-one can be described as hot, spicy, lactonic in the direction of rose or tuberose and coumarin. By comparison with the superior counterpart 8-methyl-1-oxaspiro [4.5] decan-2-one, described in the European application cited above, it can be noted that the latter compound has a less elegant, more lactonic, type note. coconut with a distinctly oily shade. On the contrary, 1- oxaspiro [4.5] decan-2-one develops a floral-type lactonic note. With greater finesse, 1-oxaspiro [4.5] decan-2-one can be used at higher concentrations than the corresponding methylated counterpart. This fact is somewhat unexpected insofar as in the series of aliphatic open chain lactones C ₈ - ₁₂ , for example, commonly used lactones in perfumery, the aggressiveness of their odor decreases with the increase in the number of carbons. A more detailed comparison between the olfactory properties of the compound of the invention and its superior counterpart will be given in the application examples described later in the text.

The proportions in which the compound of the invention can develop the desired odorous characteristics can of course vary within a very wide range of values. Those skilled in the art know from experience that such values depend on the particular effect sought as well as on the nature of the products which it is desired to flavor. We also know that these values are a function of the nature of the other constituents in a given composition when spiro-lactone (I) is used as an ingredient in a perfuming base or in a concentrate mixed with other co-ingredients, common solvents or adjuvants.

By way of example, it may be mentioned that proportions of the order of 5, 10 or even 20% by weight relative to the weight of the composition in which it is incorporated can be used without the smell of the resulting composition loses balance.

Such values can be much lower when perfuming articles such as cosmetics, soaps or detergents. The spiro-lactone (I) can be used in accordance with the invention either by direct addition to the products which it is desired to flavor in the isolated state, or more generally in mé diaper with other fragrance ingredients, additives or carriers which are widely used in perfumery. The perfume co-ingredients with which the compound of the invention can be combined in such use, belong to various chemical classes, for example aldehydes, esters, ethers and alcohols; they can be natural or synthetic.

As indicated above, spiro-lactone (I) is a known compound which can be obtained using one of the methods described in the literature, for example by radical addition of an acrylic ester to cyclohexanol in the presence of an organic peroxide. Such a reaction is illustrated by diagram A.

In the example chosen in scheme A, di-tert-butyl peroxide (DTBP) has been indicated as organic peroxide, but of course other organic peroxides may also be suitable for promoting such a radical reaction which, in itself, is well documented in the prior art.

Compared to similar products described in European Patent Application _No. 105157, the spiro lactone (I) of the invention has the advantage of being prepared from readily available products, cyclohexanol and methyl acrylate , which increases its commercial interest.

The invention is illustrated in more detail with the aid of the following examples without being limited thereto.

Example 1 Composition "Fern"

A basic composition of the "Fern" type was prepared by mixing the following ingredients (parts by weight):

To such a composition we omitted to add coumarin, traditional ingredient of a composition of this type, and instead, we added 1- oxaspiro [4.5] decan-2-one, respectively on a another sample, 8-methyl-1-oxaspiro [4.5] decan-2-one. To 88 g of the base obtained above, 12 g of 1-oxaspiro [4.5] decan-2-one were therefore added to give a new composition ("test"), while a preparation was prepared. "control" composition by adding to 88 g of the base 12 g of 8-methyl-1-oxaspiro [4.5] decan-2-one. The two new compositions were submitted to a panel of experts who considered that the "test" composition did indeed have the desired "fern" type note, while the "control" composition had a coconut-type lactonic note. . Their difference is even more marked when we double the amount of spiro-lactones added. Indeed, by adding 24 g of 1-oxaspiro [4.5] decan-2-one to the base, a new composition was obtained, the odor character of which typically remains "fern", while the addition to the base in the same proportion of 8-methyl-1-oxaspiro [4.5] decan-2-one gives a new composition whose note "coconut" becomes predominant and distorts the clean smell of the composition.

Example 2 Composition "Tuberose"

A basic composition of "Tuberose" type was prepared by mixing the following ingredients (parts by weight):

To such a composition, we omitted to add the aliphatic lactones, such as gamma-octalactone, gamma-nonalactone and gamma-decalactone, usual and traditional constituents of a composition of this type. In their place, 1-oxaspiro [4.5] decan-2-one was added, respectively, to another sample of 8-methyl-1-oxaspiro [4.5] decan-2- one, at the rate of 20 g of spirolactone for 80 g of base composition. Two new compositions were thus obtained which were subjected to an olfactory evaluation by a group of experts who expressed their opinion by declaring that the composition containing 1-oxaspiro [4.5] decan-2-one had a warm and soft, tuberose-like note, while the composition containing 8-methyl-1-oxaspiro [4.5] decan-2-one developed a sweet-floral note of lactonic type without, however, showing the desired tuberous character.

Example 3 Perfume soap

100 g of shaved soap, obtained from an unscented sodium soap base prepared with coconut oil and tallow, were mixed with, 1.0 g of 1-oxaspiro [4.5] decan 2-one until a homogeneous paste is obtained.

The soap composition thus obtained had a flowery odor.

Example 4 Scent of a solid detergent

A solid detergent base was prepared by mixing the following ingredients (parts by weight):

The addition to the detergent base of 1-oxaspiro [4.5] decan-2-one at a rate of 0.1% gives it a pleasant flowery odor.

Example 5

Adding 1-oxaspiro [4.5] decan-2- one, at a rate of 0.2%, to a sample of the softening base indicated above, gives it an elegant floral scent.

Example 6

Various consumer articles were perfumed by adding, in the proportions indicated, 1-oxaspiro [4.5] decan-2-one. To the look different articles will be indicated in the table which follows the results of the olfactory stability tests carried out by storage for one month in an oven thermostatically controlled at 40 _° of the perfumed articles obtained.

Claims (5)

1. Use of I-oxaspiro[4.5]decan-2-one as a perfuming ingredient in perfuming compositions and perfumed products.

2. Perfuming composition comprising a compound according to claim 1.

3. An ionic, anionic, non-ionic or zwitterionic detergent comprising a compound according to claim 1.

4. A deodorant of ambient air comprising a compound according to claim 1.

5. A soap comprising a compound according to claim 1.

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