EP0694604A2 - Use of 1,3-undecadien-5-yne as a perfuming ingredient - Google Patents

Abstract

1,3-undecadiene-5-yne (I) is used as a perfuming ingredient in perfume compsns. and perfumed articles. (I) is in the form of one of its (E) or (Z) isomers or mixts. of these, esp. mixts. contg. at least 50 wt.% (E)-1,3-undecadiene-5-yne.

Description

The present invention relates to the field of perfumery. It relates, more particularly, to the use of 1,3-undecadien-5-yne as a perfuming ingredient.

This compound is well known in the prior art. It has in fact been cited several times as a useful intermediary in the synthesis of 1,3,5-undecatriene and its isomers [see, for example, BP Andreini et al., Tetrahedron 43 , 4591 (1987); F. Näf et al., Helv. Chim. Acta, 58 , 1016 (1975)]. However, we did not find in these references any mention or even suggestion of the possible usefulness of this compound, or of one of its stereoisomers, for perfumery.

However, we have indeed discovered that 1,3-undecadien-5-yne and its isomers of configuration (E) and (Z) have very powerful odors and that they serve to create olfactory effects both of type floral, green and galbanum. This is how (E) -1,3-undécadién-5-yne proves to be a perfuming ingredient of choice, its odor being remarkably powerful and having a character of galbanum and fruity type, recalling the smell of the skin. mandarin, with a very marked note of the type that is characteristic of methyl octynecarbonate and methyl heptynecarbonate. It is a very pretty fragrant note, evoking the smell of violet leaves, but also having a green and fruity character reminiscent of the smell of Dynascone® [1- (5,5-dimethyl-1- cyclohexen-1-yl) -4-penten-1-one; origin: Firmenich SA, Geneva, Switzerland], while being less allylic and endowed with a more pronounced galbanum character, as well as a very clean citrus-mandarin note. The use of this compound in perfumery thus constitutes a preferred embodiment of the present invention.

For its part, (Z) -1,3-undecadien-5-yne is also a useful perfuming ingredient, its odor however being greener, with a more pronounced mastic-ocimene character.

Due to their olfactory qualities, these two compounds thus find a very varied use in perfumery, in particular for the preparation of perfuming bases and concentrates, perfumes and colognes, as well as in the perfume of articles of various consumption such as soaps, gels shower or bath, shampoos and other hair hygiene products, cosmetic preparations, body or air fresheners, or detergents or fabric softeners and cleaning products.

In these applications, they can be used either alone or, as is more common in perfumery, in admixture with other perfuming ingredients, solvents or adjuvants in common use in perfumery and which the skilled person is familiar with. even choose according to the desired effect and the nature of the product to be perfumed. A detailed description of such ingredients is superfluous here, and ingredients such as those described in reference works such as that of S. Arctander, Perfume & Flavor Chemicals, Montclair, N.J., USA (1969) can be cited as an example.

In particular, they can also be used in the form of their isomeric mixtures, in which the relative proportions (E) / (Z) can vary within a range of values between 1: 0 and 0: 1, taking all the intermediate values . According to the invention, when these mixtures of (E) -1,3-undecadien-5-yne and (Z) -1,3-undecadien-5-yne are used, those having 50% by weight or more of the first compound cited.

The concentrations in which these compounds and their aforementioned mixtures can be used to obtain the desired perfuming effects vary within a very wide range of values, it being well known that these values depend both on the nature of the article to be perfumed and on the effect fragrance sought, as well as the nature of the other co-ingredients in a given composition. Thus, concentrations of the order of 0.5 to 5%, or even 10% or more by weight of said compound, relative to the weight of the composition, are entirely suitable when the cited compounds are added to various perfume compositions. Concentrations well below these values can be used when used for the perfume of various articles such as those mentioned above.

As mentioned above, the synthesis of these compounds has been described, in particular by F. Näf et al. in the reference cited above.

The invention therefore relates to their use in perfumery as well as perfume compositions and perfumed articles containing them. It will now be described in more detail using the following examples.

Example 1 Perfuming composition

L'addition à cette composition de base de type boisé-musqué, floral, de 70 parties en poids d'une solution à 10% dans le DIPG du (E)-1,3-undécadién-5-yne lui impartit un effet à la fois vert et feuilles de violette très marqué et exalte la note fraîche de type hespéridé et notamment le caractère mandarine de la composition.A basic perfume composition was prepared by mixing the following ingredients:

The addition to this basic composition of woody-musky, floral type, of 70 parts by weight of a 10% solution in the DIPG of (E) -1,3-undécadién-5-yne gives it an effect to both green and violet leaves very marked and exalts the fresh note of citrus type and in particular the mandarin character of the composition.

Example 2 Perfume composition for fabric softener

A cette composition de base de type fleuri, rosé, poudré, violette, on a ajouté 10 parties en poids d'une solution à 10% dans le DIPG de (E)-1,3-undécadién-5-yne, pour obtenir une composition nouvelle dont la note de type floral-violette, impartie notamment par l'Iralia ® et l'α-ionone, était nettement accentuée. Par ailleurs, l'odeur de la composition était alors devenue plus verte-fruitée, avec une légère connotation liquoreuse, dont l'effet était particulièrement agréable sur du linge humide ayant été traité avec un adoucissant textile contenant, à raison de 0,1% en poids, cette composition nouvelle.A basic perfume composition intended for perfuming a fabric softener was prepared, by mixing the following ingredients:

To this basic composition of floral, pink, powdery, purple type, 10 parts by weight of a 10% solution in DIPG of (E) -1,3-undecadien-5-yne were added, to obtain a new composition whose note of floral-violet type, imparted in particular by Iralia ® and α-ionone, was clearly accentuated. Furthermore, the smell of the composition had then become more green-fruity, with a slight sweet connotation, the effect of which was particularly pleasant on damp linen having been treated with a fabric softener containing, at a rate of 0.1%. by weight, this new composition.

Claims (5)

Use of 1,3-undecadien-5-yne as a perfuming ingredient, for the preparation of a perfuming composition or of a perfumed article. Use according to claim 1, characterized in that 1,3-undecadien-5-yne is in the form of one of its isomers of configuration (E) or (Z) or of a mixture of the two. Use according to claim 2, characterized in that said mixture contains at least 50% by weight of (E) -1,3-undecadien-5-yne, relative to the weight of the mixture. Perfume composition or perfumed article resulting from the use according to one of claims 1 to 3. As a perfumed article according to claim 4, a perfume or eau de toilette, a soap, a shower or bath gel, a cosmetic preparation, a shampoo or other hair hygiene product, a body or air deodorant. environment, detergent or fabric softener, or cleaning product.