Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
1999-03-30
2002-09-10
Brouillette, Gabrielle (Department: 1721)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S022000, C512S025000, C568S376000, C568S377000, C568S367000, C568S303000
Reexamination Certificate
active
06448220
ABSTRACT:
FIELD OF THE INVENTION
This invention concerns novel fragrance compounds, and their use in perfumes and perfumed products.
SUMMARY OF THE INVENTION
In one aspect the invention provides a ketone having the structure
(as shown in
FIG. 1
) in which R is H or an alkyl group and X is a hydrocarbon group having between 4 and 12 carbon atoms, the ring being saturated or unsaturated, excluding 4-(1-ethylpropylidene)-1-cyclohexanone, 4-cyclohexylidene-1-cyclohexanone, 4-butylidene-1-cyclohex-2-enone, 4-(1-ethylpropylidene)-1-cyclohex-2-enone, 4-(2-methylpropylidene)-1-cyclohexanone, 4-cyclohexyliden-2-cyclohexen-1-one, 4-(1,5-dimethyl-4-hexenylidene)-1-cyclohexanone, 4-[4-(cyclohexyliden)cyclohexyliden]-1-cyclohexanone, 4-[4-(tert-butyl)cyclohexyliden]-1-cyclohexanone, 4-[4-(cyclohexyl)cyclohexyliden]-1-cyclohexanone, 4-(2-isopropyl-5-methylcyclohexyliden)-2-cyclohexen-1-one and 4-(3-phenylpropylidene)-1-cyclohex-2-enone.
The specifically excluded materials, namely 4-(1-ethylpropylidene)-1-cyclohexanone, 4-cyclohexylidene-1-cyclohexanone, 4-butylidene-1-cyclohex-2-enone, 4-(1-ethylpropylidene)-1-cyclohex-2-enone, 4-(2-methylpropylidene)-1-cyclohexanone, 4-cyclohexyliden-2-cyclohexen-1-one, 4-(1,5-dimethyl-4-hexenylidene)-1-cyclohexanone, 4-[4-(cyclohexyliden)cyclohexyliden]-1-cyclohexanone, 4-[4-(tert-butyl)cyclohexyliden]-1-cyclohexanone, 4-[4-(cyclohexyl)cyclohexyliden]-1-cyclohexanone, 4-(2-isopropyl-5-methylcyclohexyliden)-2-cyclohexen-1-one and 4-(3-phenylpropylidene)-1-cyclohex-2-enone, are known materials but they do not have fragrance properties that are interesting or attractive. 4-(1-ethylpropylidene)-1-cyclohexanone is disclosed in Inhoffen H. H. et al., Justus Liebigs Ann. Chem., (1964), 674, p28-35; 4-cyclohexylidene-1-cyclohexanone is disclosed in Hoogesteger F. J. et al., J. Org. Chem., (1995), 60(14), p4375-4384 and Hoogesteger, F. J. et al., J. Chem. Soc. Perkin Trans. 2, (1996), p2327-2334; 4-butylidene-1-cyclohex-2-enone is disclosed in Flemming I. et al., Tetrahedron Letters, (1979), p3209-3212; 4-(1-ethylpropylidene)-1-cyclohex-2-enone is disclosed in Inhoffen H. H. et al., Justus Liebigs Ann. Chem., (1964), 674, p28-35; 4-(2-methylpropylidene)-1-cyclohexanone is disclosed in WO 93/03012 in Example 6; 4-cyclohexyliden-2-cyclohexen-1-one is disclosed in Humphries D J et al, J. Chem. Soc. Perkin Trans. 1; 1978; p24-33 as compound 14; 4-(1,5-dimethyl-4-hexenylidene)-1-cyclohexanone is disclosed in Vig OP et al, J. Indian Chem. Soc.; 1975; vol 52, p 614-616 as compound IX; 4-[4-(cyclohexyliden)cyclohexyliden]-1-cyclohexanone and 4-[4-tert-butyl)cyclohexyliden]-1-cyclohexanone are disclosed in Hoogester F J et al, J. Org. Chem.; 1995; p4375-84 as compounds 14(2) and 21(1), respectively; 4-[4-(cyclohexyl)cyclohexyliden]-1-cyclohexanone is disclosed in Nidy EG et al, Synthesis; 1990; p1053-6 as compound 9; 4-(2-isopropyl-5-methylcyclohexyliden)-2-cyclohexen-1-one is disclosed in Flisak J R et al, J. Am. Chem. Soc.; 1990; p7299-7305 as compound 14b; and 4-(3-phenylpropylidene)-1-cyclohex-2-enone (cis and trans isomers) are disclosed in Gesson J P et al, Nouv. J. Chim., Vol. 1(6), p 511-20 as compounds 22a and 22b.
In a further aspect the invention thus provides a ketone having the structure
(as shown in
FIG. 1
) in which R is H or an alkyl group and X is a hydrocarbon group having between 4 and 12 carbon atoms, the ring being saturated or unsaturated, the ketone having fragrance properties.
The term “fragrance properties” is used to mean a discernible odour at normal room temperature (about 25° C.) that is generally regarded as interesting, pleasant or attractive.
For brevity and simplicity, materials in accordance with the invention will be referred to herein as “the ketone”, “the novel ketone” or “the ketones of the invention”.
The ketones of the invention exhibit interesting fragrance properties or odour characteristics, generally aldehydic in nature, and so may be used as such to impart, strengthen or improve the odour of a wide variety of products, or it may be used as a component of a perfume (or fragrance composition) to contribute its odour character to the overall odour of such perfume. For the purposes of this invention a perfume is intended to mean a mixture of fragrance materials, if desired mixed with or dissolved 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 indispensable or desirable. Examples of such products are: fabric washing powders, washing liquids, fabric softeners and other fabric care products; detergents and household cleaning, scouring and disinfection products; air fresheners, room sprays and pomanders; soaps, bath and shower gels, shampoos, hair conditioners and other personal cleansing products; cosmetics such as creams, ointments, toilet waters, preshave, aftershave, skin and other lotions, talcum powders, body deodorants and antiperspirants, etc.
Other fragrance materials which can be advantageously combined with a ketone according to the invention in a perfume are, 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, nitrites, 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 a ketone according to the invention are: geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenyl-ethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, trichloromethyl-phenylcarbinyl 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-cyclohex-3-enyl-carboxaldehyde, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, 4-(4-methyl-3-pentenyl)-3-cyclohexenecarboxaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptylcyclopentanone, 3-methyl-2-pentyl-2-cyclopentenone, n-decanal, n-dodecanal, 9-decenol-1, phenoxyethyl isobutyrate, phenyl-acetaldehyde dimethyl-acetal, phenylacetaldehyde diethylacetal, geranyl nitrile, citronellyl nitrile, cedryl acetate, 3-isocamphylcyclohexanol, cedryl methyl ether, isolongifolanone, aubepine nitrile, aubepine, heliotropin, coumarin, eugenol, vanillin, diphenyl oxide, hydroxycitronellal, ionones, methylionones, isomethylionones, irones, cis-3-hexenol and esters thereof, indan musks, tetralin musks, isochroman musks, macrocyclic ketones, macrolactone musks, ethylene brassylate.
Solvents which can be used for perfumes which contain a ketone according to the invention are, for example: ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
The quantities in which the ketone according to the invention can be used in perfumes or in products to be perfumed may vary within wide limits and depend, inter alia, on the nature of the product, on the nature and the quantity of the other components of the perfume in which the ketone is used and on the olfactive effect desired. It is therefore only possible to specify wide l
Brouillette Gabrielle
Morgan Lewis & Rockius LLP
Quest International B.V.
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