Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2000-01-06
2001-11-27
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S017000, C512S025000, C512S026000, C568S440000, C568S592000, C568S808000, C510S101000
Reexamination Certificate
active
06323173
ABSTRACT:
The present invention relates to the field of perfumery. More particularly, it concerns the use of alcohols of the general formula
wherein the symbols R
1
, R
2
, R
3
and R
4
represent, independently of one another, a hydrogen atom or a linear or branched, saturated or unsaturated C
1
to C
3
lower alkyl radical as perfuming ingredients.
The compounds according to the invention have odoriferous characteristics of the lily of the valley type, which are very useful in perfumery. They also have numerous advantages, such as good stability in certain aggressive media for the perfume and excellent tenacity, which makes them particularly useful and advantageous for applications in the field of functional perfumery. For this reason, they can be used in the preparation of perfumes, perfuming compositions and perfumed articles.
The alcohols of the formula (I) develop a fresh, humic, very pleasant fragrance of the lily of the valley type. This fragrance is close to that of hydroxycitronellal (7-hydroxy-3,7-dimethyloctanal), although stronger than the latter. Its character can also be described as being between that of Lilial® [3-(4-tert-butylphenyl)-2-methylpropanal] and that of Lyral® [4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde].
The compound of the formula (I), wherein R
1
, R
2
, R
3
and R
4
each represent a hydrogen atom, i.e. 2-methyl-2-indanmethanol, has a structure known per se. Its synthesis has been described in literature by J. Sonnenbichler et al, Biol. Chem. Hoppe-Seyler (1993), 374(11), 1047-55, by Shono et al, Journal of Org. Chem. (1982), 47(16), 3090-4, and by Liu et al, Tetrahedron Lett. (1979), (43), 4121-4. However, in these references there is neither a description of the fragrance of 2-methyl-2-indanmethanol, nor a suggestion of its possible use in perfumery.
Furthermore, European patent application EP 685 444 describes aldehydes, some of which have a bicyclic structure similar to that of the compounds according to the invention. 5-tert-Butyl-2-indan-carbaldehyde and 6-tert-butyl-1-indanacetaldehyde are mentioned in particular. This application refers to the odoriferous properties of these compounds and their use in the field of perfumery. Although these known compounds are more stable than other, earlier aldehydes, the alcohols of the formula (I) according to the present invention have proved to be even more stable and advantageous, while having fragrances which are just as useful and also very long-lasting. Moreover, their odoriferous properties differ from those of these known aldehydes and bring new subtleties of fragrance to the perfumer's range.
Furthermore, the compounds of the formula (I), except for 2-methyl-2-indanmethanol, are new, and the invention also relates to these compounds.
Of the compounds according to the invention, the compounds of the formula (I) in which only two symbols selected from R
1
, R
2
, R
3
and R
4
represent a hydrogen atom, the two others being different, are more highly rated, in particular 2,5,6-trimethyl-2-indanmethanol or 2,4,6-trimethyl-2-indanmethanol, which both have a floral fragrance of the lily of the valley type, evoking hints of Lilial® and hydroxycitronellal.
The compounds (I) according to the invention are also highly rated, characterised in that only one of the symbols R
1
to R
4
is other than hydrogen. In the same way, 2,4-dimethyl-2-indanmethanol also has a floral fragrance of the lily of the valley type, like 2,5-dimethyl-2-indan-methanol, a preferred compound according to the invention.
The latter has a fresh fragrance of the lily of the valley type, close to the fragrance of hydroxycitronellal (7-hydroxy-3,7-dimethyloctanal), with a very highly rated, humic, lily of the valley background note, evoking the characteristic fragrance of Mayol® (cis-7-p-menthanol; origin: Firmenich SA, Geneva, Switzerland). This compound is distinguished from hydroxycitronellal in particular by its excellent tenacity, which makes it highly valued for its use in perfumery. Its long-lasting quality has proved to be superior to that of the aforementioned known aldehydes, but it is also distinctly superior to that of Mayol® (cis-7-p-menthanol). This characteristic has been confirmed in washing, on wet and dry laundry.
The aforementioned organoleptic properties are based on the compounds present in racemic form. Owing to their structure, the compounds (I) can also be present in an optically active form and have olfactory nuances distinct from the racemic compounds, enabling different fragrances to be obtained according to the isomer used. For example, while the fragrance of (+)-2,5-dimethyl-2-indanmethanol has a floral, lily of the valley note evoking the bottom note of Lilial®, (−)-2,5-dimethyl-2-indanmethanol is closer to hydroxycitronellal.
The compounds according to the invention lend themselves just as well to use in fine perfumery, in perfumes, eaux de toilette or after-shave lotions, as to other uses common in perfumery, such as the perfuming of soaps, shower gels or bath gels, hygiene or hair care products such as shampoos, and deodorants, air fresheners and cosmetic preparations.
The compounds (I) can also be used in liquid or solid detergents for the treatment of textiles, in fabric softeners and also in detergent compositions or cleaning products for washing up or for cleaning various domestic and industrial surfaces.
In these applications, the compounds according to the invention can be used alone or mixed with other perfuming ingredients, solvents or additives commonly used in perfumery. The nature and variety of these co-ingredients do not require further description here, which in any case could not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature of the product to be perfumed and the desired olfactory effect.
These perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, nitrogenous or sulfurous heterocyclic compounds and essential oils of natural or synthetic origin. A lot of these ingredients are also listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, and in other works of a similar nature.
The proportions in which the compounds according to the invention can be incorporated into the various aforementioned products vary within a wide range of values. These values depend on the nature of the article or product that one wishes to perfume and on the desired olfactory effect, as well as the nature of the co-ingredients in a given composition when the compounds according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.
As an example, typical concentrations are in the order of 5% to 10% by weight, even 20% or more by weight, of the compounds (I) according to the invention, based on the weight of perfuming composition into which they are incorporated. Lower concentrations can be used when the compounds are applied directly in the perfuming of the various consumables mentioned hereinabove.
The invention also relates to a general process for the preparation of the compounds according to the invention, characterised by hydrogenolysis of indanone of the formula
wherein the symbols R
1
, R
2
, R
3
and R
4
are as defined for the formula (I).
This step is carried out in conditions suitable for this type of reaction, which are known to the person skilled in the art. The starting material indanone is prepared from compounds which are known or which can be obtained in a conventional manner by reaction of aldol with formaldehyde (in any one of its forms), which can be represented by the following scheme:
The compounds of the formula (II) are new compounds and form a subject of the invention.
REFERENCES:
patent: 5552379 (1996-09-01), Winter et al.
patent: 0 365 015 A2 (1990-04-01), None
patent: 0 685 444 (1995-12-01), None
patent: 2 233 645 A (1991-01-01),
Schneider Philippe
Winter Beat
Cole Monique T.
Firmenich SA
Warden Jill
Winston & Strawn
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