EP0050577A2 - Verfahren zur Herstellung parfümierender Zusammensetzungen und parfümierter Produkte und so erhaltene Zusammensetzungen und Produkte - Google Patents
Verfahren zur Herstellung parfümierender Zusammensetzungen und parfümierter Produkte und so erhaltene Zusammensetzungen und Produkte Download PDFInfo
- Publication number
- EP0050577A2 EP0050577A2 EP81420137A EP81420137A EP0050577A2 EP 0050577 A2 EP0050577 A2 EP 0050577A2 EP 81420137 A EP81420137 A EP 81420137A EP 81420137 A EP81420137 A EP 81420137A EP 0050577 A2 EP0050577 A2 EP 0050577A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- compositions
- products
- diethylheptanamide
- perfumed
- note
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 239000012437 perfumed product Substances 0.000 title claims description 4
- 239000000047 product Substances 0.000 title description 15
- 238000004519 manufacturing process Methods 0.000 title description 2
- ATMCOZCQQXIAQX-UHFFFAOYSA-N n,n-diethylheptanamide Chemical compound CCCCCCC(=O)N(CC)CC ATMCOZCQQXIAQX-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002304 perfume Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 244000178870 Lavandula angustifolia Species 0.000 description 3
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 3
- 235000006679 Mentha X verticillata Nutrition 0.000 description 3
- 235000002899 Mentha suaveolens Nutrition 0.000 description 3
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000001102 lavandula vera Substances 0.000 description 3
- 235000018219 lavender Nutrition 0.000 description 3
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- 240000005385 Jasminum sambac Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- FHJRFIYKPIXQNQ-UHFFFAOYSA-N n,n-diethyloctanamide Chemical compound CCCCCCCC(=O)N(CC)CC FHJRFIYKPIXQNQ-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- -1 heptanoyl halide Chemical class 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- KLVRKNJSKXACLQ-UHFFFAOYSA-N n,n,2-triethylbutanamide Chemical compound CCC(CC)C(=O)N(CC)CC KLVRKNJSKXACLQ-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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
Definitions
- the subject of the present invention is a process for obtaining perfume compositions and perfumed products and the compositions and products thus obtained.
- N-phenyl N-methyl ethyl-2-butanamide more or less common minty notes.
- the character of the note varies according to the nature of the substituents present on the nitrogen atom without the direction of this variation being predictable; N, N-dimethyl-2-butanamide thus has a fresh natural mint note more powerful than homologous N, N-diethylamide whose note, although mint is weaker and peppery.
- N, N-diethylcaprylamide has a different note from N, N-diethyl ethyl-2 butanamide. It follows from the above that it is difficult if not impossible for those skilled in the art to predict whether or not a given alkanamide will have a pleasant odor from an olfactory point of view and what the note will be.
- perfumers have also found that the existence of a pleasant odor for a pure product is not a sufficient condition for said product to be of interest in composition. Indeed, for a product to be used in perfumery, it must have a favorable effect on the various constituents of a composition or be compatible with them. Such an effect cannot be predicted from the proper odor of the product under consideration.
- the perfume industry is constantly looking for products which, through the originality, volume and power of their fragrance, can give the compositions in which they come in a very special character.
- the present invention relates precisely to the use, in perfumery, of such a compound.
- the subject of the present invention is a process for obtaining perfuming compositions, perfumed substances or perfumed finished products, characterized in that an effective amount is added to the usual constituents of these compositions, substances or finished products.
- the present invention also relates to perfume compositions, perfumed products and substances characterized in that they comprise, as active principle having an influence on the odor, an effective amount of N, N-diethylheptanamide.
- This formula product in fact exhales a fresh, rising, spicy odor of jasmone associated with a note of rose greenery, which make it particularly interesting in composition in bases with jasmine, peppery or lavender notes to which it confers more freshness and naturalness.
- perfume compositions mixtures of various ingredients such as • solvents, solid or liquid carriers, fixatives, various odorous compounds, etc., in which N, N-diethylheptanamide is incorporated, which mixtures are used to provide the desired fragrance to various types of finished products.
- Perfume bases constitute preferred examples of perfume compositions in which N, N-diethylheptanamide can be advantageously used.
- Another example of compositions in which this compound can be advantageously introduced, is represented by the usual detergent compositions.
- These compositions generally comprise one or more of the following ingredients: anionic, cationic or amphoteric surfactants, bleaching agents, optical brighteners, various fillers, anti-redeposition agents.
- N, N-diethylheptanamide can be added to any type of detergent composition.
- Toilet waters, aftershave lotions, perfumes, soaps or deodorant products, for example in the form of aerosols, constitute examples of substances or finished products in which N, N-diethylheptanamide brings its original note.
- N, N-diethylheptanamide is a colorless liquid, boiling at 105 ° C under a pressure of 5 mm of mercury, very soluble in the usual organic solvents such as alcohols, ketones, esters or ethers.
- the content of the compositions according to the invention in N, N-diethylheptanamide expressed as a percentage by weight in the composition considered depends on the nature of said composition (base for perfume or eau de toilette for example) and on the power and nature of the desired effect at the level of the final product. It goes without saying that in a perfume base the content of N, N-diethylheptanamide can be very high, for example greater than 50% by weight and can reach 90% by weight while in a perfume, an eau de toilette, a after shave lotion or soap, this content may be much less than 50% by weight.
- the lower limit of the content of N, N-diethylheptanamide may be that which causes a perceptible change in the smell of the fragrance or of the note of the finished product.
- this minimum content can be of the order of 0.01% by weight. It is obviously possible to use contents not included in the limits of the contents indicated above without departing from the scope of the present invention.
- N, N-diethylheptanamide can be prepared without difficulty by reacting a heptanoyl halide with diethylamine in the presence of an alkaline base in aqueous solution (soda or potash).
- N, N-diethylheptanamide reduces the indolent nature of the base and brings to the composition a fresh and finely orange note.
- N, N-diethylheptanamide attenuates the chemical side of eugenol, brings to the composition a fresh and natural spirit as well as a discreet note with a predominantly spicy note.
- N, N-diethylheptanamide brings strength, freshness and a harmonious amber-like note to the composition.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Beans For Foods Or Fodder (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT81420137T ATE9912T1 (de) | 1980-09-26 | 1981-09-21 | Verfahren zur herstellung parfuemierender zusammensetzungen und parfuemierter produkte und so erhaltene zusammensetzungen und produkte. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8020985 | 1980-09-26 | ||
FR8020985A FR2490962A1 (fr) | 1980-09-26 | 1980-09-26 | Procede d'obtention de compositions parfumantes et de produits parfumes et compositions et produits ainsi obtenus |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0050577A2 true EP0050577A2 (de) | 1982-04-28 |
EP0050577A3 EP0050577A3 (en) | 1982-09-08 |
EP0050577B1 EP0050577B1 (de) | 1984-10-17 |
Family
ID=9246440
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP81420137A Expired EP0050577B1 (de) | 1980-09-26 | 1981-09-21 | Verfahren zur Herstellung parfümierender Zusammensetzungen und parfümierter Produkte und so erhaltene Zusammensetzungen und Produkte |
Country Status (7)
Country | Link |
---|---|
US (1) | US4419281A (de) |
EP (1) | EP0050577B1 (de) |
JP (1) | JPS5785314A (de) |
AT (1) | ATE9912T1 (de) |
CA (1) | CA1172175A (de) |
DE (1) | DE3166720D1 (de) |
FR (1) | FR2490962A1 (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01250202A (ja) * | 1988-03-31 | 1989-10-05 | Hattori Seiko Co Ltd | オーナメント付メッシュバンド |
US5143900A (en) * | 1989-05-19 | 1992-09-01 | Colgate-Palmolive Company | Perfumes containing N-lower alkyl neoalkanamide (s) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1572332A (de) * | 1968-04-05 | 1969-06-27 | ||
EP0017604A1 (de) * | 1979-04-02 | 1980-10-15 | Rhone-Poulenc Specialites Chimiques | Verfahren zur Herstellung parfümierender Zusammensetzungen und parfümierter Produkte und so erhaltene Zusammensetzungen und Produkte |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4228044A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance |
-
1980
- 1980-09-26 FR FR8020985A patent/FR2490962A1/fr not_active Withdrawn
-
1981
- 1981-09-15 US US06/302,672 patent/US4419281A/en not_active Expired - Fee Related
- 1981-09-21 AT AT81420137T patent/ATE9912T1/de not_active IP Right Cessation
- 1981-09-21 EP EP81420137A patent/EP0050577B1/de not_active Expired
- 1981-09-21 DE DE8181420137T patent/DE3166720D1/de not_active Expired
- 1981-09-25 JP JP56150855A patent/JPS5785314A/ja active Granted
- 1981-09-25 CA CA000386669A patent/CA1172175A/fr not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1572332A (de) * | 1968-04-05 | 1969-06-27 | ||
EP0017604A1 (de) * | 1979-04-02 | 1980-10-15 | Rhone-Poulenc Specialites Chimiques | Verfahren zur Herstellung parfümierender Zusammensetzungen und parfümierter Produkte und so erhaltene Zusammensetzungen und Produkte |
Also Published As
Publication number | Publication date |
---|---|
JPS5785314A (en) | 1982-05-28 |
DE3166720D1 (en) | 1984-11-22 |
EP0050577B1 (de) | 1984-10-17 |
US4419281A (en) | 1983-12-06 |
ATE9912T1 (de) | 1984-11-15 |
FR2490962A1 (fr) | 1982-04-02 |
JPS6160814B2 (de) | 1986-12-23 |
EP0050577A3 (en) | 1982-09-08 |
CA1172175A (fr) | 1984-08-07 |
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