US2265437A - Perfume material - Google Patents
Perfume material Download PDFInfo
- Publication number
- US2265437A US2265437A US338218A US33821840A US2265437A US 2265437 A US2265437 A US 2265437A US 338218 A US338218 A US 338218A US 33821840 A US33821840 A US 33821840A US 2265437 A US2265437 A US 2265437A
- Authority
- US
- United States
- Prior art keywords
- hydroxycitronellal
- hydroxycitronellol
- odor
- days
- perfume
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
Definitions
- 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:
- 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:
- hydroxyc'tronellal is used in amounts the lily of the valley odor of the stabilized bydroxycitronellal as herein disclosed.
- 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...
- 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.
Description
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
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US338218A US2265437A (en) | 1940-05-31 | 1940-05-31 | Perfume material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US338218A US2265437A (en) | 1940-05-31 | 1940-05-31 | Perfume material |
Publications (1)
Publication Number | Publication Date |
---|---|
US2265437A true US2265437A (en) | 1941-12-09 |
Family
ID=23323910
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US338218A Expired - Lifetime US2265437A (en) | 1940-05-31 | 1940-05-31 | Perfume material |
Country Status (1)
Country | Link |
---|---|
US (1) | US2265437A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2993055A (en) * | 1958-10-02 | 1961-07-18 | Dow Chemical Co | 8-tert-butyl-1, 4-dioxaspiro[4.5]-decane |
US3022222A (en) * | 1958-10-02 | 1962-02-20 | Dow Chemical Co | Scent composition |
US3158644A (en) * | 1960-02-25 | 1964-11-24 | Firmenich & Cie | Alicyclic ketoesters and process for their manufacture |
US3161657A (en) * | 1960-11-05 | 1964-12-15 | Firmenich & Cie | Cyclic ether of tetrahydropyran and process for the manufacture thereof |
US3288833A (en) * | 1962-02-23 | 1966-11-29 | Firmenich & Cie | 2-alkenyl and 4-alkenyl derivatives of 3-oxo-cyclopentylacetic acid esters |
US20080241492A1 (en) * | 2005-11-25 | 2008-10-02 | Sicpa Holding S.A. | Ir-Absorbing Intaglio Ink |
-
1940
- 1940-05-31 US US338218A patent/US2265437A/en not_active Expired - Lifetime
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2993055A (en) * | 1958-10-02 | 1961-07-18 | Dow Chemical Co | 8-tert-butyl-1, 4-dioxaspiro[4.5]-decane |
US3022222A (en) * | 1958-10-02 | 1962-02-20 | Dow Chemical Co | Scent composition |
US3158644A (en) * | 1960-02-25 | 1964-11-24 | Firmenich & Cie | Alicyclic ketoesters and process for their manufacture |
US3161657A (en) * | 1960-11-05 | 1964-12-15 | Firmenich & Cie | Cyclic ether of tetrahydropyran and process for the manufacture thereof |
US3288833A (en) * | 1962-02-23 | 1966-11-29 | Firmenich & Cie | 2-alkenyl and 4-alkenyl derivatives of 3-oxo-cyclopentylacetic acid esters |
US20080241492A1 (en) * | 2005-11-25 | 2008-10-02 | Sicpa Holding S.A. | Ir-Absorbing Intaglio Ink |
US8080307B2 (en) | 2005-11-25 | 2011-12-20 | Sicpa Holding Sa | IR-absorbing Intaglio ink |
US8362130B2 (en) | 2005-11-25 | 2013-01-29 | Sicpa Holding Sa | IR-absorbing Intaglio ink |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3325369A (en) | Perfume compositions containing geranonitrile, cinnamyl nitrile or 2-nonenyl nitrile | |
SU814283A3 (en) | Aromatizing composition | |
GB798901A (en) | 4-tert.-butyl-alpha-methyl-hydrocinnamic aldehyde | |
US3637533A (en) | Perfume-containing compositions containing certain oximes as olfactory agents | |
US2265437A (en) | Perfume material | |
US2976321A (en) | Para-tertiary-butylhydrocinnamic aldehyde | |
US2154341A (en) | Stabilization of fatty acid compounds | |
US3548006A (en) | Aldehydes useful in perfumery | |
US2889254A (en) | Soaps and other perfumed compositions containing dihydroterpinyl acetate | |
CN108300608B (en) | Long-acting fragrance-retaining composition, perfume and laundry detergent | |
US2918412A (en) | Perfume oils containing 3-methyl-1-nonyn-3-ol | |
US3847975A (en) | Perfume compositions containing substituted cyclohexane compounds | |
US3673120A (en) | Perfumery compositions containing patchouli oil and 8-camphene carbinol | |
ES406234A1 (en) | Perfumed compositions | |
US2371623A (en) | Method of preserving soap and resulting product | |
US3185629A (en) | Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal | |
US3942761A (en) | 4-(2'-Norbornyl)-2-butanones | |
DE2835445A1 (en) | USE OF ESTER OF THE MIXTURE OF THE MIXTURE OF THE TRICYCLO CORNER CLAMP TO 5.2.1.0 HIGH 2.6 CORNER CLAMP TO DECAN-3 AND TRICYCLO CORNER CLAMP TO 5.2.1.0 HIGH 2.6 CORNER CLAMP TO DECAN-4-CARBONIC ACID AS A FRAGRANT, AS WELL AS THESE OXIDE | |
MX2015004976A (en) | Improvements in or relating to organic compounds. | |
US4419282A (en) | N,N-Dimethyloctanamide fragrances | |
DE2015865A1 (en) | Cyclic esters and use (of the same) in perfumes | |
US2333655A (en) | Antioxidant for fats and oils | |
US4267075A (en) | Perfume compositions containing esters of 3,5,5-trimethylhexanoic acid | |
US1878102A (en) | Finger nail detergent | |
US2324347A (en) | Preservation of perfumes |