US3461085A - Perfume composition containing styrene derivatives - Google Patents
Perfume composition containing styrene derivatives Download PDFInfo
- Publication number
- US3461085A US3461085A US556279A US3461085DA US3461085A US 3461085 A US3461085 A US 3461085A US 556279 A US556279 A US 556279A US 3461085D A US3461085D A US 3461085DA US 3461085 A US3461085 A US 3461085A
- Authority
- US
- United States
- Prior art keywords
- perfume
- styrene derivatives
- composition containing
- perfume composition
- styrene
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
Definitions
- a perfume composition uses as an olfactory ingredient in a perfume carrier.
- R is methyl or ethyl and R is branched or nonbranched alkyl having 3-5 carbon atoms.
- the preferred species of ingredient in the carrier is [3,2-dimethyl-5-isopropyl styrene.
- the present invention relates to perfume compositions and novel components thereof that serve as olfactory ingredients.
- the olfactory ingredients of perfume compositions with which the present invention is concerned have the general formula in which R is methyl or ethyl and R is a branched or straight chain alkyl group containing 3-5 carbon atoms, and which may be propyl, isopropyl, butyl, isobutyl, tert.- butyl, pentyl, isopentyl, or the like.
- the preferred group for R is isopropyl.
- the present invention comprises the discovery that the above group of styrene derivatives, especially 6,2-dimethyl S-isopropyl styrene, have high odor value per se and in perfume compositions.
- perfume compositions of course includes not only perfumes which are applied as such, but also the other compositions in which perfumes are incorporated such as cosmetics, soaps, lotions, aerosols, creams, powders, and the like.
- the invention also comprises the discovery of a number of new species of the above genus, which are new per se and which also possess the above desirable perfume characteristics.
- styrene derivatives of the above group exist in stereo-isomeric forms, depending on the orientation of the methyl and the hydrogen that are attached at the fl-position. Both transand cis-isomers but especially the former have the properties of the present invention.
- perfume compositions according to the present invention are as follows.
- Hyacinth composition Parts by weight Isoamyl salicylate 34( Phenylethyl alcohol 25( Cinnamic alcohol 15[ Citronellol 10( Phenylacetaldehyde dimethylacetal 5( Hydratropic aldehyde 3( [3,2-dimethyl S-isopropyl styrene 2f Petitgrain oil L 2f Citronellyl acetate 2i Galbanum oil Petitgrain composition: Parts by weight Menthanyl acetate 250 Linalyl acetate 200 Linalool 200 Geraniol 150 u-Terpineol 65 ,8-Methyl Z-ethyl -isopropyl styrene 50 Geranyl acetate 5O l-limonene 35 EXAMPLE I-II Verveine composition: Parts by weight Oil of lemon grass rect.
- a perfume composition comprising an effective amount of a compound of the formula as an olfactory ingredient in a perfume carrier, in which R is methyl or ethyl and R is branched or nonbranched alkyl having 3-5 carbon atoms.
- a perfume composition comprising as an olfactory ingredient an effective amount of ,8,2-dirnethyl '5-isopropyl styrene in a perfume carrier.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Description
United States Patent US. Cl. 252-522 2 Claims ABSTRACT OF THE DISCLOSURE A perfume composition uses as an olfactory ingredient in a perfume carrier. R is methyl or ethyl and R is branched or nonbranched alkyl having 3-5 carbon atoms. The preferred species of ingredient in the carrier is [3,2-dimethyl-5-isopropyl styrene.
The present invention relates to perfume compositions and novel components thereof that serve as olfactory ingredients.
The olfactory ingredients of perfume compositions with which the present invention is concerned have the general formula in which R is methyl or ethyl and R is a branched or straight chain alkyl group containing 3-5 carbon atoms, and which may be propyl, isopropyl, butyl, isobutyl, tert.- butyl, pentyl, isopentyl, or the like. The preferred group for R is isopropyl.
One species of the above genus is in the prior art per se but not as an olfactory material. This is the species in which R is methyl and R is isopropyl, namely, 5,2- dimethyl S-isopropyl styrene (R. Lalande and J. P. Pillion in C. R. Acad. Sci. Paris, 258 (1964), No. 6, 1830-2).
The present invention comprises the discovery that the above group of styrene derivatives, especially 6,2-dimethyl S-isopropyl styrene, have high odor value per se and in perfume compositions.
As the odors are reminiscent of vetivert, galbanum, and angelica oil, the styrene derivatives as mentioned above are very valuable in perfumery. They can be blended with other perfume constituents to obtain specific perfume compositions having widely varying characteristics. As used herein, the term perfume compositions of course includes not only perfumes which are applied as such, but also the other compositions in which perfumes are incorporated such as cosmetics, soaps, lotions, aerosols, creams, powders, and the like. The invention also comprises the discovery of a number of new species of the above genus, which are new per se and which also possess the above desirable perfume characteristics.
Accordingly, it is an object of the present invention to 3,461,085 Patented Aug. 12, 1969 provide perfume compositions and novel components thereof, which are relatively simple and inexpensive to manufacture and which have high odor value and desirable blending properties with other perfume components.
The styrene derivatives of the above group exist in stereo-isomeric forms, depending on the orientation of the methyl and the hydrogen that are attached at the fl-position. Both transand cis-isomers but especially the former have the properties of the present invention.
To prepare the above styrene derivatives, there may be conducted a Friedel-Crafts reaction between a suitable compound having the formula and propionyl chloride, thereby to produce an aromatic ketone having the formula R and R being as described above. The ketone is reduced to the corresponding carbinol having the formula which is in turn dehydrated with acid to the styrene having the formula first given above. This is the method described by Lalande and Pillion, supra, for the production of 5,2- dimethyl S-isopropyl styrene; and specifically B-methyl Z-ethyl S-isopropyl styrene may be produced by the use of l-ethyl 4-isopropyl benzene; while ,8,2-dimethy1 5-tert.- butyl styrene may be produced by using 1-methyl 4-tert.- butyl benzene as the starting material, it being understood that the other species may be produced by using the corresponding di-substituted benzene as the starting material.
Examples of perfume compositions according to the present invention are as follows.
EXAMPLE I Hyacinth composition: Parts by weight Isoamyl salicylate 34( Phenylethyl alcohol 25( Cinnamic alcohol 15[ Citronellol 10( Phenylacetaldehyde dimethylacetal 5( Hydratropic aldehyde 3( [3,2-dimethyl S-isopropyl styrene 2f Petitgrain oil L 2f Citronellyl acetate 2i Galbanum oil Petitgrain composition: Parts by weight Menthanyl acetate 250 Linalyl acetate 200 Linalool 200 Geraniol 150 u-Terpineol 65 ,8-Methyl Z-ethyl -isopropyl styrene 50 Geranyl acetate 5O l-limonene 35 EXAMPLE I-II Verveine composition: Parts by weight Oil of lemon grass rect. 350 Citral 100% 280 Geraniol 100 Methyl ionone 75 Lemon oil messina, C.P. 70 Benzyl acetate 50 ,8,2-dimethyl 5-tert.-butyl styrene 25 Hydroxycitronellal 25 Citronellal Neroline bromelia 10 From a consideration of the foregoing disclosure, it will be evident that the initially recited object of the present invention has been achieved.
What we claim is:
1. A perfume composition comprising an effective amount of a compound of the formula as an olfactory ingredient in a perfume carrier, in which R is methyl or ethyl and R is branched or nonbranched alkyl having 3-5 carbon atoms.
2. A perfume composition comprising as an olfactory ingredient an effective amount of ,8,2-dirnethyl '5-isopropyl styrene in a perfume carrier.
References Cited Lalande et al.: C. R. Acad. Sci., Paris, vol. 258, N0. 6, February 1964, pp. 1830-1832.
ALBERT T. MEYERS, Primary Examiner VERA C. CLARKE, Assistant Examiner U.S. Cl. X.R. 260669
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL6507579A NL6507579A (en) | 1965-06-14 | 1965-06-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3461085A true US3461085A (en) | 1969-08-12 |
Family
ID=19793376
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US556279A Expired - Lifetime US3461085A (en) | 1965-06-14 | 1966-06-09 | Perfume composition containing styrene derivatives |
Country Status (7)
Country | Link |
---|---|
US (1) | US3461085A (en) |
JP (1) | JPS5145657B1 (en) |
BE (1) | BE682163A (en) |
CH (1) | CH476832A (en) |
DE (1) | DE1617014B1 (en) |
GB (1) | GB1117797A (en) |
NL (2) | NL6507579A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090137450A1 (en) * | 2005-09-23 | 2009-05-28 | Roger John Henry Duprey | Perfume Compositions |
-
0
- NL NL125892D patent/NL125892C/xx active
-
1965
- 1965-06-14 NL NL6507579A patent/NL6507579A/xx unknown
-
1966
- 1966-06-06 BE BE682163D patent/BE682163A/xx unknown
- 1966-06-07 GB GB25294/66A patent/GB1117797A/en not_active Expired
- 1966-06-09 US US556279A patent/US3461085A/en not_active Expired - Lifetime
- 1966-06-10 DE DE1966N0028660 patent/DE1617014B1/en active Pending
- 1966-06-14 JP JP41038058A patent/JPS5145657B1/ja active Pending
- 1966-06-14 CH CH853866A patent/CH476832A/en not_active IP Right Cessation
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090137450A1 (en) * | 2005-09-23 | 2009-05-28 | Roger John Henry Duprey | Perfume Compositions |
US7713922B2 (en) * | 2005-09-23 | 2010-05-11 | Quest International Services B.V. | Perfume compositions |
Also Published As
Publication number | Publication date |
---|---|
NL6507579A (en) | 1966-12-15 |
NL125892C (en) | |
GB1117797A (en) | 1968-06-26 |
CH476832A (en) | 1969-08-15 |
JPS5145657B1 (en) | 1976-12-04 |
DE1617014B1 (en) | 1971-02-25 |
BE682163A (en) | 1966-12-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2875131A (en) | 4-tert.-butyl alpha-methyl hydrocinnamic aldehyde | |
US3637533A (en) | Perfume-containing compositions containing certain oximes as olfactory agents | |
US4252986A (en) | Fixative for perfume compositions | |
US3296080A (en) | Linalool homologues | |
JPH08319250A (en) | Perfume | |
US4313855A (en) | Fixative for perfume compositions | |
US3461085A (en) | Perfume composition containing styrene derivatives | |
US4544714A (en) | Odorant oximes | |
US3258400A (en) | Isopropyl and diisopropyl-3, 4-dihydrocoumarins in perfume compositions | |
CA1116180A (en) | Odorant dialkylcyclohexane acetates | |
US3185629A (en) | Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal | |
US3673120A (en) | Perfumery compositions containing patchouli oil and 8-camphene carbinol | |
US3598745A (en) | Substituted 4,7-methanoindenes perfume compositions | |
US3764567A (en) | Perfume composition | |
US4426321A (en) | Odorant alkadienyl ketones, alcohols and oximes | |
US4011177A (en) | Chemicals and their use in perfumery | |
EP0191365B1 (en) | Araliphatic oximes, process for their production and perfume compositions containing such compounds | |
JP2000514104A (en) | Nitrile | |
US3268594A (en) | Dimethyl acetals of alpha, beta acetylenic aldehydes | |
US4119575A (en) | Polycyclic alcohol perfume compositions | |
DE1617021B1 (en) | Perfume set | |
JPS6020364B2 (en) | long lasting fragrance | |
US20030153485A1 (en) | Trimethyldecenyl compounds | |
US5163453A (en) | 3,5,5,6,8,8,-hexamethyl-1,2,3,4,5,6,7,8,-octahydro-2-naphthalenone | |
DE69604821T2 (en) | BASIC PERFUME COMPILATION |