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Publication numberUS2265437 A
Publication typeGrant
Publication dateDec 9, 1941
Filing dateMay 31, 1940
Priority dateMay 31, 1940
Publication numberUS 2265437 A, US 2265437A, US-A-2265437, US2265437 A, US2265437A
InventorsFiore Alphonse T, Max Luthy
Original AssigneeBurton T Bush Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Perfume material
US 2265437 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

Patented Dec. 9, 1941 2.265.437 I PERFUME MATERIAL Max Luthy, Ridgewood, and Alphonse T. Flore,

Passaic,

N. J., assignors to Burton '1'. Bush,

Inc.,

New York, N. Y., a corporation New Jersey No Drawing. Application May 31, 1940.

Serial No. 338,218

4 Claims.

lCl. 167-94) This invention deals with improvements in the perfumery art. More particularly, it relates to perfume compositions containing hydroxycitronellal and hydroxycitronellol. Some examples of such compositions are cosmetics, toilet and laundry soaps, and perfumes.

The object of this invention is to provide perfume ingredients containing hydroxycitronellal in a relatively stable form. A further object is to obtain a stabilized hydroxycitronellal whose lily of the valley odor has not been materially modified from that of the unstabilized hydroxycitronellal. Another object is to provide a stabilized hydroxycitronellal capable of effectively masking the undesirable soapy odor in soap and at the same time imparting a pleasant lily of the valley scent thereto. A still further object of this invention is to furnish new products for use in the perfumery arts. Other objects will be apparent to those skilled in the art from the description.

Hydroxycitronellal is a liquid having a very pronounced odor and is widely used in perfumery.- Its probable structural formula is:

I 011.11 VH| o The alternate formulae are given because it is not known whether hydroxycitronellal has one of its hydroxyl groups in the No. 2 or No. 3 position, or whether it is a mixture of both such products whose formulae are above given. Unfortunately, much of the odor value of hydroxycitronellal is soon lost in use. failing of aldehydes and has been attributed generally to the formation of the corresponding acids by reason .of oxidation.

We have discovered that the desirable properties of hydroxycitronellal can be practically uti lized in perfumes, soaps, etc. by adding hydroxycitronellol thereto. The latter has been prepared by hydrogenating hydroxycitronellal and is described in the co-pending application of M. S. Carpenter, S. N. 337,834, filed May 29, 1940. It is a colorless and somewhat viscous oil having a very faint odor and characterized by the following physical data:

Boiling point 140 C. at 3 mm. mercury Specific gravity at 25 C./25 C 0.930 Refractive index 11. 1.460

This is a general number representing the fraction 0 ronellal are brought into contact, even at room temperatures.

The stabilizing effect of hydroxycitronellolon hydroxycitronellal was tested as follows:

50 grams of the sample to be tested were placed in a Petri dish. The latter was allowed to stand uncovered at room temperature, 1. e. 20-25 C. The acid number of each sample was taken at the start oi the test and after 4, 8and 12 days.

The following tables illustrate the changeshinacid number of the samples with passage of time and show the effect of hydroxycitronellol.

' Table I Composition Acid values Sample H d H d 2 y roxyy toxyl citronellal citroncllol 1mm] days days days It") 0 7. 4 41. 5 66. 5 101. 5 85 15 5. 2 27. 6 42. 5 65. 0 25 4. 6 l9. 8 29. 6 45. 3 D 50 50 3.6 8.4 11.9 22.8 1. 25 75 2. 6 3. 2 5. 0 5. 8 F 15 2. l 2. 3 2. 5 3. 8 o o 1. 4 1. a 1:6 1. 1

' Table II Calculated acid value of hydroxycitrunellal Sample Initial 4 days 8 days 12 days 7.4 41.5 66.5 101.5 5. 9 32. 2 49. 7 76. 5 5. 65 25. 9 39. 0 59. 7 5. S 15. 3 22. 2 44. 0 5, 0 8. 35 15. 2 l8. 0 6. 05 6. 9 7. 6 l5. 7

These data were obtained by subtracting the product of the corresponding acid-value of hydroxycitronellol (G) and the figure representing the fraction of the sample cons1st1ng of hydroxyutronellol from the acid value of the sample (Table I) and dividing this figure by'the the sample consistmg of hydroxycitronellal.

These results show clearly the inhibiting effect of hydroxycitronellol on the oxidation of hydroxycitronellal. Whereas one gram of the latter has an acid number of 101.5 after 12 days exposure under the test conditions, it would have a calculated acid number of only 44.0 after the same period and under the same conditions if 1 proved by the lol. The odor retention or such soaps as well as the soap.

- not only acts as a The importance of gram oI-hydroxycitronellol were added to it initially, i. e. at the start of the test.

Soaps which .contain hydroxycitronelial as a perfume ingredient have certain properti% imincorporation of hydroxycitronelthe color stability and tendency to resist rancidity are enhanced. Although other amounts of hydroxycitronellol impart desirable characteristics, we prefer to use between 25 and 75% of hydroxycitronellol based onthe combined weight 01' the 'hydroxycitronellol-hydrowoitronellal. In

practice, hydroxyc'tronellal is used in amounts the lily of the valley odor of the stabilized bydroxycitronellal as herein disclosed.

It is understood that the invention is to be construed as broadly as permissible in view of the prior claims.

What we claim as new is:

l. A perfume composition containing hydroxycitronellal and hydroxycitronellol to stabilize the hydroxycitronellal against air oxidation.

2. A perfume ingredient consisting of hydroxycitronellal and hydroxycitronellol to stabilize the same against air oxidation, said ingredient being characterized by its lily of the, valley odor...

v 3. A perfume composition having hydroxycitronellal and hydroxycitronellolto stabilize the hydroxycitronellal against air oxidation, the hydrozwcitronellol being present in an ranging from 25% to of the combined weight of hydroxycitronellol and hydroxycitronv ellal. I

4; A perfume ingredient consisting. of 75 to 25 parts by weight of hydroxycitronellal and 25 to 75 parts by weight of hydroxycitronellol to sta bilize the hydroxycitronellal against air oxidation, said ingredient being characterized by its lily of the valley odor. y

Lurmr. mnonsn'r. moan.

art, limited solely by the appended amount

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2993055 *Oct 2, 1958Jul 18, 1961Dow Chemical Co8-tert-butyl-1, 4-dioxaspiro[4.5]-decane
US3022222 *Jun 27, 1960Feb 20, 1962Dow Chemical CoScent composition
US3158644 *Feb 24, 1961Nov 24, 1964Firmenich & CieAlicyclic ketoesters and process for their manufacture
US3161657 *Nov 3, 1961Dec 15, 1964Firmenich & CieCyclic ether of tetrahydropyran and process for the manufacture thereof
US3288833 *Feb 18, 1963Nov 29, 1966Firmenich & Cie2-alkenyl and 4-alkenyl derivatives of 3-oxo-cyclopentylacetic acid esters
US8080307Nov 16, 2006Dec 20, 2011Sicpa Holding SaIR-absorbing Intaglio ink
US8362130Nov 18, 2011Jan 29, 2013Sicpa Holding SaIR-absorbing Intaglio ink
Classifications
U.S. Classification512/2, 568/421, 510/101
International ClassificationC11B9/00
Cooperative ClassificationC11B9/0015
European ClassificationC11B9/00B4