Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
1999-10-25
2001-11-06
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S023000, C512S022000, C568S821000, C568S822000, C568S838000, C510S101000
Reexamination Certificate
active
06313087
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to 3-alkyl-cyclopentan-1-ols, cyclohexan-1-ols and cycloheptan-1-ols, to their use as fragrance materials and to perfumes and perfumed products comprising these alcohols.
BACKGROUND TO THE INVENTION
In the perfumery art there is a continuous interest in new fragrance materials, on the one hand caused by a continuous need for compounds with a new odour character and on the other hand caused by the fact that many of the long Known materials have come under scrutiny lately because of certain undesirable properties. Thus, some well known fragrance materials have been criticized because of their potential instability in some applications. Some of these are well known floral fragrances, such as &agr;-hexylcinnamaldehyde, 2-methyl-3-(p-tert-butylphenyl)propanal, 2-methyl-3-(p-isopropylphenyl)propanal, 3-(p-tert-butylphenyl)propanal and hydroxycitronellal.
Some alkyl substituted cyclohexanols are long known in perfumery. Thus, S. Arctander, Perfume and Flavor Chemicals mentions: 4-isopropyl-, 4-tert.butyl-, 4-tert.amyl-, 4-heptyl-, 4-ethyl- and 2-methyl-4-tert.amyl-cyclohexanol (monograph no's 2692, 433, 165, 1531, 1201 and 1749). The odour character of all five compounds is overridingly woody with camphoraceous, piney, vetiver and cedar notes, and often also dry with tarry or leathery odour notes. 2-Tert.butylcyclohexanol (monogr.no. 432) is also described as dry woody, camphoraceous and tarry.
Certain 4-isoamylcyclohexanols, particularly di-, tri- and tetra-methyl substituted ones are disclosed in U.S. Pat. No. 4,400,545 as fragrance materials with baisamic, woody, sweet, rooty, musty, earthy and leathery odours.
4-(C8-Alkyl)-cyclohexanols are disclosed in EP 0 005 196 as having an odour resembling that of 4-tert.butyl-cyclohexanol, but less strong. The most important compound is 4-(2,2,3,3tetramethylbutyl)cyclohexanol.
In Japanese patent application JP 02131405 (Hasegawa Koryo Co. Ltd) 2-, 3- and 4-alkylcycloalkanols and esters thereof are described as cockroach repellents. In passing it is stated that these compounds are used as fragrances, but for the alcohols this is not further substantiated than by referring to the Arctander monographs cited above, and no indication of odour character is given in this patent application.
In EP 0 053 979 alkyl substituted 3-(2-alkenyl)cyclopentanols are broadly disclosed with a wide variety of odour notes of the floral, fruity and woody type reminiscent of rose, muguet, bergamot, cucumber, hay-like, dry-woody, cedar or vetiver. The specific compounds shown are all unsubstituted 3-(2-alkenyl)cyclopentanols and 1,2,2-trimethyl-3-(2-alkenyl)cyclopentanols.
In U.S. Pat. No. 4,277,618 1-methyl-2-(C4alkyl)cyclohexanols (C4=sec.butyl or tert.butyl) are disclosed as intermediates in the synthesis of the corresponding acetates. Only the latter are said to be fragrance materials.
In U.S. Pat. No. 3,769,330 1-ethyl-2-(C4-alkyl)cyclohexanols (C4=n.butyl, isobutyl, sec.butyl or tert.butyl) are disclosed as fragrance materials with a woody odour.
It has now been found that 3-alkylcycloalkanols of the formula I below are valuable fragrance materials with strong floral odours with citrus and/or rhubarb and sometimes herbal notes. The floral odour is particularly characterized by its overriding muguet character. The citrus notes are sometimes reminiscent of grapefruit.
SUMMARY OF THE INVENTION
In one aspect the invention thus provides a perurne comprising fragrance materials known in the art and at least one alcohol according to Formula I:
wherein R1 represents hydrogen or a methyl, ethyl or propyl group; R2, R4 and R5 independently represent hydrogen or a methyl group; R3 represents a saturated hydrocarbon group with 4-8 carbon atoms, provided that the first carbon atom of this hydrocarbon group is not a tertiary carbon atom; n represents the numbers 1, 2 and 3.
The compounds in which R1 is methyl, ethyl or propyl are novel per se.
Preferably R1 is hydrogen or a methyl or ethyl group, more preferably it is methyl or ethyl.
Preferably R5 is hydrogen, more preferably R2 and R5 are both hydrogen, most preferably R2, R4 and R5 are all hydrogen.
Preferably R3 is an alkyl group which comprises at least one secondary carbon atom or a cyclopentyl, cyclohexyl or cycloheptyl group; more preferably, if R3 is an alkyl group, C-atom 2 or 3 (counted from the C-atom attached to the ring) is a secondary carbon atom. Most preferably R3 is cyclohexyl, isobutyl or isoamyl.
Preferably n is 2 or 3, more preferably n is 2.
Thus, the invention provides perfumes and perfumed products comprising the alcohols according to Formula I. Furthermore, the invention provides a process for imparting a floral odour note, more particularly a muguet-type odour note, to perfumes and products specified above.
The alcohols according, to the invention may be used as such in a wide variety of products, or they may be used as components of a perfume to contribute their floral odour. This odour note does not necessarily need to be the strongest or predominant odour note in the perfume or the final perfumed product, but it clearly contributes to the overall odour of such perfume or perfumed product.
For the purposes of this invention a perfume is defined as a mixture of fragrance materials, if desired mixed with or dissoved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or any product for which an agreeable odour is indispensible or desirable. The alcohols according to the invention and the perfumes containing them are particularly suitable for use in e.g.: fabric washing powders, washing liquids, fabric softeners and other fabric care products; soaps, bath and shower gels, shampoos, hair conditioners and other personal cleansing products; cosmetic products such as creams, ointments, toilet waters, products for preshave or aftershave use, skin and other lotions, talcum powders, body deodorants and antiperspirants.
Other fragrance materials known in the art which can be advantageously combined with an alcohol according to the invention in a perfume, for example, natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., but also synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds.
Such fragrance materials are mentioned, for example, in S. Arctander, Perfume and Flavor Chemicals (Montclair, N.J., 1969), in S. Arctander, Perfume and Flavor Materials of Natural Origin (Elizabeth, N.J., 1960) and in “Flavor and Fragrance Materials—1991” Allured Publishing Co. Wheaton, Ill. USA.
Examples of fragrance materials which can be used in combination with an alcohol according to the invention are: geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol, dihydrornyrcenyll acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate., 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, trichloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, &agr;-hexylcinnamaldehyde, 2-methyl-3-(p-tert-butylphenyl)propanal, 2-methyl-3-(p-isopropylphenyl)propanal, 3-(p-tert-butylphenyl)propanal, 2,4-dimethyl-3-cyclohexenylcarboxaldehyde, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, 4-(4methyl-3-pentenyl)-3-cyclohextenecarboxaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptylcyclopentanone, 3-methyl2-pentyl-2-cyclopentenone, n-decanal, n-dodecanal, 9-decen-1-ol, phenoxyethyl isobutyrate, phenylacetaldehyde dimethylacetal, phenylacetaldehyde diethylacetal, seranyl nitrile, citronellyl nitrile, cedryl acetate, 3-isocamphylcyclohexanol, cedr
Cole Monique T.
Pillsbury & Winthrop LLP
Quest International BV
Warden Jill
LandOfFree
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