US2889254A - Soaps and other perfumed compositions containing dihydroterpinyl acetate - Google Patents

Description

United States Patent 'SOAPS AND OTHER PERFUNIED COL [POSITIONS CONTAINING DIHYDROTERPINYL ACETATE Alphonse T. Fiore, Teaneck, Garry C. Kitchens, Packanack Lake, and Harry C. Saunders, Nutley, N.J., assignors to The Givaudan Corporation, New York, N .Y., a corporation of New Jersey No Drawing. Application July 12, 1956 Serial No. 597,359

3 Claims. (Cl. 167-94) This invention relates to soaps, such as toilet soap, and other perfumed compositions containing dihydroterpinyl acetate.

An object of this invention is to provide a toilet soap having the following odor qualities: good stability, freshness and naturalness (as opposed to a chemical odor).

Another object is to provide a toilet soap having an odor which is clean and pleasant such as is obtained from the ester components of important natural soap odorants, e.g., lavender oil, petitgrain oil, and bergamot oil, and yet not having the roughness and undesirable pine-like character associated with synthetic esters.

Another object of this invention is to furnish perfumed compositions containing a low-cost readily available synthetic ingredient which resembles the oils of bergamot and petitgrain.

Other objects of our invention will become apparent from the following description.

We have attained the foregoing and other objects by incorporating dihydroterpinyl acetate into toilet soap and other perfumed compositions. We have found that amounts of dihydroterpinyl acetate from about 0.02 to 1.5% by weight of the total soap give satisfactory results and that amounts from 0.1 to 0.6% on the same basis give excellent results.

In using dihydroterpinyl acetate as a substitute or extender for oil of petitgrain it has been found that the acetate can be used up to and including 40% by weight of the petitgrain oil-dehydroterpinyl acetate mixture.

Artificial 'bergamot oils can be made by using from 5 to 75% by weight of di'hydroterpinyl acetate on the basis "of the total mixture. We prefer to use amounts from 40 to 60% on the same basis.

Artificial oil of petitgrain containing from 5 to 65% by weight of dihydroterpinyl acetate on the basis of the total mixture can be made. However, We prefer to use amounts from 30 to 45% on the same basis.

In using our novel perfume ingredient the usual practices of the perfumer may be employed. For this .reason specific instructions concerning the method of formulating toilet soap and other perfumed compositions containing dihydroterpinyl acetate are unnecessary here.

Dihydroterpinyl acetate has already been described in the literature. To the best of our present knowledge it was first described in 1910 by M. A. Bhal and M. A. Heller in Compt. rend, 150, 1762-65.

However, in spite of the fact that dihydroterpinyl acetate has already been known for over 45 years and the fact that terpinyl acetate has been known for a long time for its olfactory properties, no one until now recognized the unique olfactory properties of dihydroterpinyl acetate. It may well be that the reason for this omission stems from the fact that the closely-related linalyl acetate is weakened in odor qualities when it is hydrogenated. It was therefore surprising to us that we found that the odor of dihydroterpinyl acetate is not only as strong as that of terpinyl acetate but the Patented June 2, 195.9

Specific gravity, 25 C./25 C. 09328-09337 Refractive index, 20 C. 1.4493-1.4495

Purity percent.. -100 EXAMPLE I Soap cakes were made as follows:

Twenty grams of standard No. 1 soap pellets and 10.1 gram of perfuming agent were milled together in a Coors No. 522- r porcelain mortar until they were reduced to a fine homogeneous powder. Two grams of distilled water were added and the mixture was milled again to a plastic mass. The soap thus prepared was charged into a cylindrical tableting die which when pressed by a hand arbor-press produced a soap cake 3.8 cm. in diameter and 2.0 cm. thick. In separate cakes made as just described was incorporated the same specifled portions of dihydroterpinyl acetate, terpinyl acetate and linalyl acetate. The cakes were then exposed to air and daylight indoors for a period of 6 months and examined about once a month.

The cake containing the dihydroterpinyl acetate maintained a strong, fresh odor during the entire period. The cake containing the terpinyl acetate weakened after two months and faded completely after three months. The cake containing the linalyl acetate turned rancid or sour smelling after two months.

EXAMPLE II A soap perfume was formulated using dihydroterpinyl acetate as an ingredient. The formula is as follows:

Soap perfume N0. 1

Soluble resin Styrax (10% in diethyl phthalate)- 8 This perfume was incorporated in milled toilet soap at the rate of 1% in the same manner as described in Example I. It covered the odor of the soap well and gave a pleasant refreshing odor to the soap.

EXAMPLE III Another soap perfume was formulated containing a,

larger proportion of dihydroterpinyl acetate. is as follows:

Its formula Soap perfume N0. 2

This perfume was incorporated in soap at the rate of 1% in a manner as described in Example I and found to give a good cover to the soap odor and a pleasant clean odor.

EXAMPLE IV Compositions containing oil of petitgrain and 10, 20, 30, 40, 50, 60 and 70% dihydroterpinyl acetate by weight of the total mixture were prepared. Similar series containing oil of petitgrain and other synthetic extenders such as terpinyl acetate and nopyl acetate (6,6- dimethylbicyclo-[1,1,31-hept-2-ene-2 ethyl acetate) were prepared.

The petitgrain mixtures containing the other synthetic extenders possessed a distracting piney note which was not evident in the petitgrain mixture containing dihydroterpinyl acetate.

Those petitgrain mixtures, containing dihydroterpinyl acetate had more realistic petitgrain oil odor than the mixture containing the other petitgrain extenders at like concentrations.

EXAMPLE V An artificial bergamot was formulated using 70% of dihydroterpinyl acetate as the main ester component. Following is its formula:

Bergamot type Dihydroterpinyl acetate 600 Oil sweet orange cold pressed California 30 Methyl benzoate 20 N-decanal (10% in diethyl phthalate) 3 Camphene 16 Geranyl formate 60 Coumarin crystals N.F. 2 p-Isopropylacetophenone 26 Terpineol 40 2-methylundecanal-1 (10% in diethyl phthalate) 1 Peppermint rectified oil 5 v 4 Soluble resin galbanum 10% Estragon oil 10% in diethyl phthalate) 14 Bay leaves oil 2 Lemon oil California 3 'y-Undecalactone (10% in diethyl phthalate) l Soluble resin labdanum (10% in diethyl phthalate) 2 Soluble resin olibanum 5 Benzaldehyde (1% in diethyl phthalate) 20 EXAMPLE VI An artificial oil of petitgrain was formulated. The following is the formula:

Dihydroterpinyl acetate 200 Dipentine 60 Camphene 40 Myrcene 24 Citronellol 10 Geranyl acetate 20 Methyl anthranilate 4 3-cyclohexylpropanone-2 l6 Furfural 1 N-decanal (10% in diethyl phthalate) 2 Amyl benzoate 8 Bay leaves oil 1.5 Thyme oil white 1.5 Rue oil 2.5 p-Cresyl acetate 1.5 Fennel oil sweet 1 While we have described our invention in detail in its preferred embodiment, it will be obvious to those skilled in the art, after understanding our invention, that various changes and modifications may be made therein without departing from the spirit or scope thereof. We aim in the appended claims to cover all such modifications and changes.

We claim:

1. Toilet soap containing a minor amount of dihydroterpinyl acetate sufficient to impart to said soap odor stability, freshness and naturalness.

2. Toilet soap, containing from about 0.02% to about 1.5% by weight of dihydroterpinyl acetate, said soap being characterized by odor stability, freshness and naturalness imparted thereto by said ester.

3. A perfume composition comprising oil of petitgrain and as an extender therefor, dihydroterpinyl acetate, the latter being present in an amount up to about 40% by weight of the total weight of said oil of petitgrain and said extender.

References Cited in the file of this patent Behal: Comptes Rendus, tome 150, June 1910, pp. 17624.

Simonsen: The Terpenes, Cambridge Univ. Press, vol. 1, 2nd ed., revised 1953, pp. 253, 254, 262.

Wertheim: Textbook of Organic Chcm., the Blakiston Co., Philadelphia, 2nd ed., 1946, pp 50, 52.

in diethyl phthalate) 6

Claims (1)

1. TOILET SOAP CONTAINING A MINOR AMOUNT OF DIHYDROTERPINYL ACETATE SUFFICIENT TO IMPART TO SAID SOAP ODOR STABILITY, FRESHNESS AND NATURALNESS.