Cleaning compositions for solid surfaces – auxiliary compositions – With oxygen – halogen – sulfur – or nitrogen containing or... – Ring in the component
Reexamination Certificate
1999-07-12
2001-02-13
Douyon, Lorna M. (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
With oxygen, halogen, sulfur, or nitrogen containing or...
Ring in the component
C510S108000, C510S119000, C510S152000, C510S276000, C510S367000, C510S394000, C424S076100, C424S076400, C424S401000, C044S275000, C512S022000, C514S844000, C560S001000
Reexamination Certificate
active
06187727
ABSTRACT:
This invention relates to the use of 2-methyl-3-cyclohexylpropanol and esters thereof, particularly the acetate, as perfumery materials.
BACKGROUND OF THE INVENTION
Many compounds have been described in the literature as fragrance materials. As is the case with many classes of compounds having varied utilities, of the many compounds that are known to possess pleasing fragrance notes, only a very small portion are utilized commercially. There are several reasons for this, notably toxicological constraints, environmental considerations, biodegradability, performance, and cost effectiveness. While all of these factors must be carefully weighed in consideration of whether to introduce a new fragrance material, perhaps the most critical are performance and cost. Performance properties include odor activity, notes, and aesthetics; substantivity; and solubility. The cost effectiveness involves manufacture costs and the amount of the compound required to impart fragrance to a consumable product. Of course, the lower the amount of fragrance material required, the higher its cost effectiveness. Many materials have met some of the above-mentioned criteria, yet have not been successful because of cost versus performance.
It must further be borne in mind that, because fragrance materials are by nature utilized in comparatively small quantities, only a very few benefit from the cost efficiency of large-scale production. All of these factors, combined with the tendency in many countries to take a more rigid regulatory position concerning ingredients in consumable products, have acted to hamper the introduction of new fragrance materials in recent years.
There is an on-going need for new fragrance materials that can be readily synthesized from relatively inexpensive raw materials, meet the criteria set forth above, possess unique fragrance notes and, perhaps most importantly, are cost-effective in use. Such materials are provided in accordance with the present invention.
SUMMARY OF THE INVENTION
The invention relates to the use of 2-methyl-3-cyclohexylpropanol, its esters, particularly the acetate and mixtures thereof as fragrance materials.
DETAILED DESCRIPTION OF THE INVENTION
The compounds found to possess attractive fragrance properties in accordance with the present invention are 2-methyl-3-cyclohexylpropanol, and certain of it esters. 2-Methyl-3- cyclohexylpropanol has the structural formula:
2-Methyl-3-cyclohexylpropanol is known in the literature, but there has been to date neither recognition of its fragrant properties nor suggestion that it may possess such properties. 2-Methyl-3-cyclohexylpropyl acetate is a novel compound as are the other esters of 2-methyl-3-cyclohexylpropanol disclosed herein.
2-Methyl-3-cyclohexylpropanol has been disclosed in a series of patents by Sipos assigned to Johnson & Johnson, e.g. U.S. Pat. No 4,091,090 and Australian Patent No. 534,455, as a penetration enhancer and potentiator for topically applied medicaments such as anesthetics and antivirals. The preparation of 2-methyl-3-cyclohexylpropanol for use in optical relation studies was disclosed by Levene and Marker, J. Biol. Chem. Vol. 110, pages 299-309 (1935). The preparation of 2-methyl-3-cyclohexylpropanol in optically pure form via chiral benzopyranoisoxazolidines has been disclosed by Abiko et al., Chem. Int. Ed. Engl. Vol. 34, pages 793-395 (1995). None of these publications gives any suggestion that 2-methyl-3-cyclohexylpropanol or its ester might possess fragrant properties.
2-Methyl-3-cyclohexylpropanol is conveniently prepared by hydrogenation of 2-methyl-3-phenylpropanol, a known material that can be conveniently prepared by the hydrogenation of 2-methyl-3-phenyl-1-propen-1-ol, which is commercially available (e.g., from Aldrich Chemical Co.). While 2-Methyl-3-phenylpropanol is the preferred substrate, (&agr;-methyl cinnamaldehyde, or, &agr;-methyl dihydrocinnamaldehyde may also be used as the starting material. Hydrogenation of phenyl rings is well known in the art and the particular method for accomplishing the above transformation is not critical. Those of ordinary skill in the art will readily appreciate that temperature, solvent, catalyst, pressure and mixing rate are all parameters that effect the hydrogenation and how the relationships among them may be adjusted to effect the desired conversion, reaction rate, selectivity, and apparatus limitations.
The above hydrogenation is preferably carried out in a solvent at elevated temperatures and pressures over a suitable active metal hydrogenation catalyst. Acceptable solvents, catalysts, apparatus, and procedures for aromatic hydrogenation can be found in Augustine, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Decker, New York, N.Y. (1996), incorporated herein by reference. Many hydrogenation catalysts are effective, including, without limitation, palladium, platinum, copper chromite, copper, rhodium, ruthenium and the supported versions thereof. Supported catalysts are preferred because the active metal is used more efficiently. Supported nickel is the preferred catalyst. Preferred supports include alumina, silica, carbon, titania, and kieselguhr, with silica and alumina being particularly preferred. While the weight percent of nickel on the support is not critical, it will be appreciated that the higher the metal weight percent the faster the reaction. Generally the nickel weight percent will range from about 5 to about 95%, preferably 25 to 75%, and most preferably 45 to 65%.
The temperature, amount of supported nickel catalyst, and hydrogenation hydrogen pressure are interrelated. The preferred temperature is from about 50° to 500° C., more preferably from about 100° to about 300° C., and most preferred from about 140° to 200° C. According to these temperature parameters, the amount of metal is preferably about 0.01 to 10 weight percent—relative to the weight of the total reaction mixture—preferably 1 to 5%, most preferably 2 to 3% by weight. The hydrogen pressure is preferably about 50 to about 5000 psi, more preferably about 100 to 1000 psi, and most preferably about 200 to 700 psi. Useful solvents include those well known in the art of hydrogenation, such as, hydrocarbons, ethers, and alcohols. Alcohols are most preferred, particularly lower alkanols such as methanol, ethanol, propanol, butanol, and pentanol. Most preferred is to use no added solvent, i.e., the substrate and product alcohols function as solvents.
The esters of 2-methyl-3-cyclohexylpropanol in accordance with the present invention are represented by the following structure:
wherein R is a straight- or branched-chain, saturated or unsaturated hydrocarbon radical having from 1 to 24 carbon atoms. Those esters wherein the hydrocarbon radical represented by R contains from 1 to 6 carbon atoms are fragrance materials in accordance with the present invention. Preferred in this group are those esters of the above formula wherein R is a hydrocarbon radical having from 1 to 3 carbon atoms, particularly the acetate. Those esters wherein the hydrocarbon radical represented by R contains from 7 to 24 carbon atoms are also fragrance materials, but are actually sustained release forms of 2-methyl-3-cyclohexylpropanol. Preferred in this group are those esters of the above formula wherein R represents a saturated or unsaturated hydrocarbon radical having 7 to 10, particularly 7 or 8, carbon atoms. Such sustained release fragrances are particularly suited for perfuming a fabric washed with a lipase-containing detergent. In use, the lipase hydrolyzes the ester thereby slowly releasing 2-methyl-3-cyclohexylpropanol onto the fabric.
Another form of ester that likewise acts as a sustained release for 2-methyl-3-cyclohexylpropanol in similar laundry products is a diester represented by the formula
(C
6
H
11
)—CH
2
—CH(CH
3
)—CH
2
—O—C(O)—(CH
2
)n—(O)C—O—CH
2
—CH(CH3)—CH
2
—(C
6
H
11
)
wherein n is an integer from 0 to 6. Such diesters are hydrolyzed by lipase in the same manner to release 2-methyl-3-cyclohexylpropanol. A particularly preferred diester in accordance with
Frank Walter C.
Pagano Alex R.
Bush Boake Allen Inc.
Douyon Lorna M.
Gibbons Del Deo Dolan Griffinger & Vecchione
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