US3461085A - Perfume composition containing styrene derivatives - Google Patents

Description

United States Patent US. Cl. 252-522 2 Claims ABSTRACT OF THE DISCLOSURE A perfume composition uses as an olfactory ingredient in a perfume carrier. R is methyl or ethyl and R is branched or nonbranched alkyl having 3-5 carbon atoms. The preferred species of ingredient in the carrier is [3,2-dimethyl-5-isopropyl styrene.

The present invention relates to perfume compositions and novel components thereof that serve as olfactory ingredients.

The olfactory ingredients of perfume compositions with which the present invention is concerned have the general formula in which R is methyl or ethyl and R is a branched or straight chain alkyl group containing 3-5 carbon atoms, and which may be propyl, isopropyl, butyl, isobutyl, tert.- butyl, pentyl, isopentyl, or the like. The preferred group for R is isopropyl.

One species of the above genus is in the prior art per se but not as an olfactory material. This is the species in which R is methyl and R is isopropyl, namely, 5,2- dimethyl S-isopropyl styrene (R. Lalande and J. P. Pillion in C. R. Acad. Sci. Paris, 258 (1964), No. 6, 1830-2).

The present invention comprises the discovery that the above group of styrene derivatives, especially 6,2-dimethyl S-isopropyl styrene, have high odor value per se and in perfume compositions.

As the odors are reminiscent of vetivert, galbanum, and angelica oil, the styrene derivatives as mentioned above are very valuable in perfumery. They can be blended with other perfume constituents to obtain specific perfume compositions having widely varying characteristics. As used herein, the term perfume compositions of course includes not only perfumes which are applied as such, but also the other compositions in which perfumes are incorporated such as cosmetics, soaps, lotions, aerosols, creams, powders, and the like. The invention also comprises the discovery of a number of new species of the above genus, which are new per se and which also possess the above desirable perfume characteristics.

Accordingly, it is an object of the present invention to 3,461,085 Patented Aug. 12, 1969 provide perfume compositions and novel components thereof, which are relatively simple and inexpensive to manufacture and which have high odor value and desirable blending properties with other perfume components.

The styrene derivatives of the above group exist in stereo-isomeric forms, depending on the orientation of the methyl and the hydrogen that are attached at the fl-position. Both transand cis-isomers but especially the former have the properties of the present invention.

To prepare the above styrene derivatives, there may be conducted a Friedel-Crafts reaction between a suitable compound having the formula and propionyl chloride, thereby to produce an aromatic ketone having the formula R and R being as described above. The ketone is reduced to the corresponding carbinol having the formula which is in turn dehydrated with acid to the styrene having the formula first given above. This is the method described by Lalande and Pillion, supra, for the production of 5,2- dimethyl S-isopropyl styrene; and specifically B-methyl Z-ethyl S-isopropyl styrene may be produced by the use of l-ethyl 4-isopropyl benzene; while ,8,2-dimethy1 5-tert.- butyl styrene may be produced by using 1-methyl 4-tert.- butyl benzene as the starting material, it being understood that the other species may be produced by using the corresponding di-substituted benzene as the starting material.

Examples of perfume compositions according to the present invention are as follows.

EXAMPLE I Hyacinth composition: Parts by weight Isoamyl salicylate 34( Phenylethyl alcohol 25( Cinnamic alcohol 15[ Citronellol 10( Phenylacetaldehyde dimethylacetal 5( Hydratropic aldehyde 3( [3,2-dimethyl S-isopropyl styrene 2f Petitgrain oil L 2f Citronellyl acetate 2i Galbanum oil Petitgrain composition: Parts by weight Menthanyl acetate 250 Linalyl acetate 200 Linalool 200 Geraniol 150 u-Terpineol 65 ,8-Methyl Z-ethyl -isopropyl styrene 50 Geranyl acetate 5O l-limonene 35 EXAMPLE I-II Verveine composition: Parts by weight Oil of lemon grass rect. 350 Citral 100% 280 Geraniol 100 Methyl ionone 75 Lemon oil messina, C.P. 70 Benzyl acetate 50 ,8,2-dimethyl 5-tert.-butyl styrene 25 Hydroxycitronellal 25 Citronellal Neroline bromelia 10 From a consideration of the foregoing disclosure, it will be evident that the initially recited object of the present invention has been achieved.

What we claim is:

1. A perfume composition comprising an effective amount of a compound of the formula as an olfactory ingredient in a perfume carrier, in which R is methyl or ethyl and R is branched or nonbranched alkyl having 3-5 carbon atoms.

2. A perfume composition comprising as an olfactory ingredient an effective amount of ,8,2-dirnethyl '5-isopropyl styrene in a perfume carrier.

References Cited Lalande et al.: C. R. Acad. Sci., Paris, vol. 258, N0. 6, February 1964, pp. 1830-1832.

ALBERT T. MEYERS, Primary Examiner VERA C. CLARKE, Assistant Examiner U.S. Cl. X.R. 260669