Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2003-03-25
2004-05-11
Keys, Rosalynd (Department: 1621)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S009000, C512S023000, C512S025000, C510S104000, C510S506000, C568S665000, C568S667000
Reexamination Certificate
active
06734159
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
Industrially prepared perfume oils nowadays consist for the greatest part of synthetic fragrances.
2. Description of the Related Art
Although the traditional use of essential oils and extracts of a vegetable and animal origin continues to play an important role in the field of alcoholic (fine) perfumery, the perfuming of laundry detergents, soaps, household cleaners and similar technical products requires the use of fragrances which satisfy the technical requirements with regard to stability and substantivity. In order to correspond with these particular requirements, perfumes for use in technical consumer goods are largely formulated from synthetic fragrances. However, because these perfumes are needed in large amounts, all of the important perfume houses and fragrance manufacturers of aroma substances have in the last few decades directed their research activities to the preparation of novel synthetic fragrances.
In the meantime, synthetically prepared fragrances which in the past have been prepared essentially for technical use because of their comparatively low price and their high stability, have increasingly been used in fine perfumery as well.
Meanwhile there is a constant need for fragrances with improved properties, such as odor quality, stability, skin compatibility and environmental compatibility. For the purposes of a good ecobalance, products are strived for here which are based on renewable raw materials.
One raw material of natural origin which is available in relatively large amounts is the sesquiterpene longifolene (1), which occurs as the main component in Indian turpentine oil and as a secondary component in numerous other types of turpentine oil and other essential oils. Even more than 2 decades ago a number of secondary products from longifolene had been prepared and the fragrance properties thereof described. G. Ohloff reports in his book “Riechstoffe und Geruchssinn” [Fragrances and Sense of Smell] [Springer-Verlag, 1990, ISBN No. 3-540-52560-2, pages 87-88] in summary that at least 4 commercial fragrances are derived from (+)-longifolene (1), and 13 fragrance derivatives can be commercially utilized from the isolongifolene (2) accessible therefrom by isomerization. Some of these derivatives are given the characteristic odor type woody (odor of wood) by Ohloff; other odor notes are not mentioned.
The chemistry and odor properties of the commercially important derivatives of isolongifolene (2) have been reported by G. Färber and H. Tan [G. Färber, Parfümerie+Kosmetik, 68, 18 (1987), H. Tan, Parfümerie+Kosmetik, 67, 564 (1986)]. In this connection, the last-named publication in particular reveals that the isolongifolene derivatives known as fragrance can be used instead of the known wood scent note because of their woody character.
Our publication EP-A 0 543 470 describes cyclic isolongifolanone ketals of the general formula B
(in which wavy lines are &agr;- and &bgr;-configuration, and R and R′ are hydrogen or methyl or ethyl radicals). These ketals are valuable fragrances which have strong woody odor properties with floral-fresh effects and velvety moss/ambergris character.
Our publication EP-A 0 669 308 describes isolongifolanole derivatives of the general formula C
(in which wavy lines are &agr;- and &bgr;-configuration, and R1 is hydrogen or methyl radicals and R2 is methyl or ethyl radicals). These derivatives likewise have woody olfactory properties.
GB-A 1 505 821 describes isolongifolanole and lower esters thereof (acyl groups with up to 6 carbon atoms) as fragrances, the &agr;-/&bgr;-isometry of the hydroxyl or carboxyl function being discussed. Said fragrances have strong woody odor properties reminiscent of cedryl acetate and vetiveryl acetate and are particularly highly suitable for perfume compositions with floral or citrus-woody character.
GB-A 1 256 535 describes the controlled oxidation of isolongifolene (2) to isolongifolenone (3) and subsequent reduction thereof to isolongifolenol (4). The subsequent esterification (acyl groups having up to 5 carbon atoms) of the virtually odorless isolongifolenol (4) again leads to fragrances (isolongifolenyl esters) with a woody odor profile.
According to the prior art just given, the field of longifolene and isolongifolene derivatives appears to have been investigated particularly thoroughly. In addition to a limited number of longifolene and isolongifolene derivatives with valuable fragrance properties (cf. in particular the abovementioned prior art), there is an utterly confusingly large number of derivatives of the abovementioned sesquiterpenes described in the literature or synthesized and investigated by ourselves which are of little or no significant olfactory value.
Even if some of the known isolongifolene derivatives have excellent olfactory properties and can be prepared on an industrial scale in a manner which is both low in cost and also environmentally compatible, it would nevertheless, looking at the group of isolongifolene derivatives as a whole, increasingly be perceived as disadvantageous and restrictive that for isolongifolenol derivatives with a noteworthy olfactory activity, a woody aspect frequently is in the foreground, which limits the use spectrum of the derivatives.
SUMMARY OF THE INVENTION
It was therefore the primary object of the present invention to provide a fragrance, preferably an isolongifolene derivative or a group of isolongifolene derivatives, and a process for the preparation thereof, where, compared with the isolongifolene derivatives of olfactory interest mentioned before, at least not only the woody, but also other odor aspects should be in the foreground. Advantageously, the nonwoody aspects should be dominant here.
In connection with this, a further object was to provide a perfume composition whose olfactory properties are codetermined by a fragrance, preferably an isolongifolene derivative or a mixture of isolongifolene derivatives, for which at least not only woody but also other odor aspects are in the foreground.
Further objects on which the present invention is based can be formulated as follows: The isolongifolene derivative or the mixture of isolongifolene derivatives should as far as possible be able to contribute to a long-lasting after-odor and to a good fixing of a perfume composition.
The isolongifolene derivative or the mixture of isolongifolene derivatives should as far as possible be able to contribute in a perfume composition to a rounding off and harmonizing of the main note (the “bouquet”).
Finally, a further object of the present invention was to provide a process with which a material (a substance) can have added to it a (not primarily woody) odor or have its (intrinsic) odor intensified, by adding an isolongifolene derivative or a mixture of isolongifolene derivatives to the material (the substance).
Finally, a further object of the present invention was to provide a process with which a material (a substance) can have added to it a (not primarily woody) odor or have its (intrinsic) odor intensified, by adding an isolongifolene derivative or a mixture of isolongifolene derivatives to the material (the substance).
There is particularly great interest in this connection in fragrances with a musk character. The isolongifolene derivatives used hitherto as fragrances do not usually have a musk character of this type. To prepare perfume oils with a musk note, it is therefore necessary to mix one of the known musk fragrances with the respective isolongifolene derivative.
Thus, for example, the already mentioned GB-A 1 256 535, inter alia, recommends mixing the isolongifolenol esters described therein with a musk compound, such as musk ketone or ethylene brassylate.
In the likewise already mentioned GB-A 1 505 821, musk compounds are likewise among the preferred compounds for mixing with the disclosed isolongifolene derivatives.
The situation is similar also with regard to the compounds disclosed in our own specified publications.
DETAILED DE
Pickenhagen Wilhelm
Schatkowski Dietmar
Keys Rosalynd
Pendorf & Cutliff
Symrise GmbH & Co. KG
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