Perfume compositions – Perfume compositions – Ring containing active ingredient
Patent
1997-12-10
1999-03-30
Reamer, James H.
Perfume compositions
Perfume compositions
Ring containing active ingredient
549364, A61K 746
Patent
active
058889612
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase of international application PCT/EP96/00930, filed Mar. 4. 1996 which designated the U.S.
FIELD OF THE INVENTION
This invention concerns a novel 1,3-dioxane and its use in perfumes and perfumed products.
BACKGROUND OF THE INVENTION
Various 1,3-dioxanes, also designated as cyclic acetals derived from an aldehyde and a 1,3-diol, are known in the perfumery literature.
Thus, in U.S. Pat. No. 4,146,506 perfume compositions comprising a 4-isopropyl-5,5-dimethyldioxane with an C1-C3 alkyl substituent in the 2 position have been described. The 1,3-dioxanes are said to have odour notes ranging from fruity, herbal to woody.
In EP 0 039 029 2-(1'-methylbutyl)-1,3-dioxanes are described which are substituted in the 4 and 5 position with at least 2 and in many cases 3 alkyl groups with a maximum total number of carbon atoms of 6. The compounds are said to have floral and fruity odour notes.
In NL-A-7305487 2-n.butyl-4,4,6-trimethyl-1,3-dioxane is described as having lavender, minty and laurel leaf odour notes. Also described therein are various other 4,4,6-trimethyl-1,3-dioxanes, some of which from S. Arctander, Perfume and Flavor Chemicals, Montclair, N.J., 1969, others from own evaluation. The judgement of their suitability for perfumery is mixed.
In NL-A-7305488 various 2-substituted 4-propyl-5-ethyl-1,3-dioxanes are described, again with mixed opinion as to their suitability for perfumery.
In NL-A-7415594 various 2,4 substituted 1,3-dioxanes (erroneously described as 2,6 substituted) are described, in particular 2-(4'-methylpent(en)yl)-4-methyldioxanes, as having woody, floral and fruity (citrussy) odour notes.
In DE-A-2334378 2-(2'-methyl-1'-propenyl)-1,3-dioxanes with one or more methyl or ethyl groups in the positions 4 and/or 5 and/or 6 are described as having a rose-like odour reminiscent to rose oxide.
Finally, in GB 981,285 various substituted 1,3-dioxanes are described in which the 2 position must be substituted with a C4-C9 alkyl group and the 4 position with a methyl group. These substitution requirement are stressed as importand for obtaining the desired geranium-rose odour.
SUMMARY OF THE INVENTION
The present invention provides the cyclic acetal 2-isobutyl-5-methyl-1,3-dioxane as well as perfume compositions and perfumed products comprising this compound in olfactively effective amounts.
DETAILED DESCRIPTION OF THE INVENTION
The novel acetal of the invention has attractive odour qualities, which may be described as a strong chamomile and fruity odour with anisseed, minty, camphor and green notes. This is unexpected, particularly in view of the rose-oxide like odour of the compounds described in DE-A-2334378
The dioxane according to the invention is a powerful fragrance material which 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 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 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. 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 the dioxane 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 hyd
REFERENCES:
patent: 3423430 (1969-01-01), Cahn et al.
Quest International B.V.
Reamer James H.
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