US2918412A - Perfume oils containing 3-methyl-1-nonyn-3-ol - Google Patents

Description

=3. Names-l United States Patent O ce PERFUME OILS CONTAINING 3-METHYL-1- NONYN-S-OL Thomas F. Wood, Little Falls, N.J., assignor to The Givaudan Corporation, New York, N.Y., a corporation of New Jersey No Drawing. Application November 9, 1955 Serial No. 546,005

1 Claim. (Cl. 167--94) This invention relates to perfume-containing compositions, and more especially to such compositions as cosmetic creams, detergent soaps, perfume oils and the like, which contain 3-methyl-1-nonyn-3-ol.

As is well known, many ingredients used in perfumery have natural origins, i.e., they are obtained from a natural source. In many cases the source is a distant one. As a result, the products obtained from such sources are often characterized by non-uniformity as regards not only composition but also as regards prices, which fluctuate over wide ranges, and availability, which is affected by political upheavals and local and general wars. An example of a widely-used perfume ingredient which has a natural source is linalool.

An object of this invention is to provide a synthetic substitute for the naturally-occurring linalool. A further object is to provide replacement for linalool which has desirable olfactory properties and at the same time can be made at a relatively inexpensive cost and in ample amounts. Other objects of this invention will be apparent from the following description.

In accordance with my invention I utilize 3-methyl-lnonyn-3-ol as an olfactory ingredient in perfume-contain ing compositions such as cosmetic creams, detergent soaps, perfume oils and the like The term perfume-containing compositions herein is intended to mean perfume oils, cosmetic creams and detergent soap.

The amounts of 3-methyl-1-nonyn3-ol employed difier according to the desires of the compounder and the nature of the composition. been found that, in general, a cosmetic cream having from about 0.01 to about 0.8 percent by weight of 3- methyl-'1-nonyn-3-ol on the weight of the finished cream gives satisfactory results, amounts from about 0.1% to about 0.3% being especially satisfactory. Detergent soaps having from about 0.01 to about 0.5 percent by weight of 3-methyl-l-nonyn-3-ol on the'weight of the finished bar of soap give desirable results, amounts from about 0.1 to about 0.2 percent giving especially desirable results. Perfume oils having from about 1.0 to about 80 percent of 3-methyl-l-nonyn-3-ol on the weight formula total are satisfactory, amounts from about 20 to about percent being recommended in general.

The novel perfume ingredient herein-disclosed has been described in the scientific literature. In this connection reference is made to the following citationsfor methods of preparing the S-methyl-l-nonyn-B-ol: Compt. rend., 234,.1557-9 (1952); J.A.C.S., 69, 239-41 (1947); and US. Patent 2,385,547.

The novel ingredient for the purposes of this invention may be incorporated in perfume-containing compositions in the conventional manner and hence no special directions are thought to be necessary here.

The compositions containing 3-methyl-1-nonyn-3-ol have imparted to them a light, highly-diffusing floral character without any resultant discoloration being caused by the 3-methyl-1-nonyn-3-ol.

For purposes of illustration it has- In order further to clarify my invention, the following 2,918,412 Patented Dec. 22, 1959 examples are given, it being understood that they are for purposes of illustration and not for purposes of limitation.

Example I 0.2 gram of 3-methyl-l-nonyn-3-ol was incorporated into 20.0 grams of white milled toilet soap by weighing the soap and 3-methyl-1-nonyn-3-ol, milling them together in a porcelain mortar until they are intimately combined, adding to them 2.0 gms. of distilled water, further milling until the mixture has a homogeneous plastic consistency and then compressing this mass into a soap cake by means of a stainless steel tablet-forming die and a hand arbor press.

The soap had a light but fresh floral odor which remained stable for more than 10 months exposed to air and daylight. The color of the soap also remained the same throughout this 10 month period.

Example II A cosmetic cream was made by melting 12 grams of beeswax in 46 grams of mineral oil. Forty grams of a solution of 1 gram of borax in 39 grams of water were added slowly to the beeswax-mineral oil melt. The mixture was stirred continuously while being allowed to cool to 50 C.

1.0 gram of 3-methyl1-nonyn-3-ol was added to this cream which was stirred until the 3-,methyl-1-nonyn-3-ol was intimately combined with it.

The resulting cream was cooled to room temperature and was found to have a stable light floral odor. The cream did not discolor upon standing at room temperature for 10 months.

Example III A perfume oil having a jasmin character was made by mixing together the following ingredients in the amounts given:

Grams 3-methyl-1-nonyn-3-ol 100 Benzyl acetate 200 Amyl cinnamic aldehyde 28 Phenyl ethyl alcohol 100 Hydroxy citronellal 200 Phenoxy ethyl iso butyrate p-Cresyl phenyl acetate 28 Indole 1% in benzyl benzoate 22 Phenyl acetaldehyde 50% 10 Cedryl acetate distilled 8 Naphthalene 6 N-decanal 10% diethyl phthalate 1 Phenyl propyl aldehyde 2 Oil cade 3 Oil peppermint 2 Oil thyme red 3 Oil cedarleaf 3 Soluble resin galbanum 2 Example IV A perfume oil having a honeysuckle character was Grams Phenyl acetaldehyde 50% 6 Phenyl acetic acid 4 Oil petitgrain l8 Soluble resin olibanum 6 Geranium bourbon 7 Methyl anthranilate 2 Cedrenol 2 Vanillin 2 Oil red thyme 1 Example V A perfume oil having a rose character was made by mixing together the following ingredients in the amounts given:

Example VI A perfume oil having an orange blossom character was made by mixing together the following ingredients in the amounts given:

Grams 3-methy1-1-nonyn-3-ol 200 Nerol 120 Phenyl ethyl alcohol 80 Hydroxy citronellal 40 Methyl anthranilate 46 Amyl benzoate 32 Oil bergamot 40 Geranyl formate 20 Benzyl acetate 20 Indole 4 Phenyl acetic acid 4 N-decanal in diethyl phthalate 4 Oil estragon 2 Soluble resin balsam Peru 3 Methyl acetophenone 2 Oil peppermint 4 Oil Caraway 6 Oil cade 1 Oil citronella-ceylon 1 Example VII A perfume oil having a lilac character was made by mixing together the following ingredients in the amounts given:

Grams Undecalactone 2 Oil spearmint 8 Soluble resin galbanum 1 Oil patchouly 3 Oil nutmeg 3 Pine needle Siberian 4 Oil cade 5% in alcohol 4 Example VIII A perfume oil having the character of coriander oil was made by mixing together the following ingredients in the amounts given:

Grams 3-methyl-l-nonyn-3-ol 520 p-Cymene Phellandrene 24 N-decanal 4 Borneol technical 8 Benzyl iso amyl ether 8 N-nonanol 6 Furfuryl acetate 5 Oil star anise 3 Siberian pine needles 3 Citronella Ceylon 2 Oil cumin 2 Coumarin 4 Example IX A perfume oil having the character of cinnamon oil was made by mixing together the following ingredients in the amounts given:

Example X A perfume oil having the character of Bois de Rose oil was made by mixing together the following ingredients in the amounts given:

' Grams 3-methyl-1-nonyn-3-ol 2600 Terpineol p 200 Myrcene Terpinolene 50 Dipentine 50 p-Methyl acetophenone 10 Geraniol 31 Furfural 5 Resin olibanum 15 Oil spike lavender 15 Oil peppermint 25 Oil lemongrass native 20 Oil rue 27 While I have described my invention in detail in its preferred embodiments, it will be obvious to those skilled in the art that various changes and modifications may be made therein, in particular in the actual formulations employed, without departing from the spirit or scope thereof. I aim in the appended claim to cover all such medificatien and ch I claim:

A perfume oil having 3-methy1-1-nonyn-3-ol as an olfactory ingredient.

References Cited in the file of this patent UNITED STATES PATENTS 2,385,547 Smith Sept. 25, 1945 2,815,379 Surmantis Dec. 3, 1957 2,824,896 Surmantis Feb. 25, 1958 Press, Ltd., London, 1949, pp. 13- 20, 24, 123, 124, 5 242-249.

Am. Perf., v01. 18, 1924, pp. 621-626.