EP0017604A1 - 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
- EP0017604A1 EP0017604A1 EP80420040A EP80420040A EP0017604A1 EP 0017604 A1 EP0017604 A1 EP 0017604A1 EP 80420040 A EP80420040 A EP 80420040A EP 80420040 A EP80420040 A EP 80420040A EP 0017604 A1 EP0017604 A1 EP 0017604A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compositions
- products
- note
- ethyl
- perfumed
- 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 33
- 238000000034 method Methods 0.000 title claims description 4
- 239000012437 perfumed product Substances 0.000 title claims description 4
- 239000000047 product Substances 0.000 title description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000002304 perfume Substances 0.000 claims description 12
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 abstract description 8
- LYGCLXFQIQORSE-UHFFFAOYSA-N n,n,2-triethylhexanamide Chemical compound CCCCC(CC)C(=O)N(CC)CC LYGCLXFQIQORSE-UHFFFAOYSA-N 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 235000006679 Mentha X verticillata Nutrition 0.000 description 4
- 235000002899 Mentha suaveolens Nutrition 0.000 description 4
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 244000297179 Syringa vulgaris Species 0.000 description 3
- 235000004338 Syringa vulgaris Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 244000004281 Eucalyptus maculata Species 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- 240000005385 Jasminum sambac Species 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 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
- 239000004615 ingredient Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 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
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 1
- -1 2-ethylhexanoyl halide Chemical class 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 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
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- XLCGTKDLMYYKMD-UHFFFAOYSA-N n,2-diethylhexanamide Chemical compound CCCCC(CC)C(=O)NCC XLCGTKDLMYYKMD-UHFFFAOYSA-N 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
- FHJRFIYKPIXQNQ-UHFFFAOYSA-N n,n-diethyloctanamide Chemical compound CCCCCCCC(=O)N(CC)CC FHJRFIYKPIXQNQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 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
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005406 washing Methods 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.
- the amides of C 5 -C 6 alkanoic acids have, with the exception of N-phenyl N-methyl ethyl-2 butanamide, more or less common minty notes.
- N, N-dimethyl-2-butanamide thus has a fresh natural mint note more powerful than the homologous N, N-ethyl amide whose note, although mint is weaker and peppery.
- N, N'-diethylcaprylamide has a different note from N, N-diethyl ethyl-2 butanamide.
- 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 perfume compositions, perfumed substances or perfumed finished products characterized in that an effective amount is added to the usual constituents of these compositions, substances or products of N, N-diethyl ethyl-2 hexanamide.
- the present invention also relates to perfuming compositions, perfumed products and substances characterized in that they contain, as active principle having an influence on the odor, an effective amount of N, N-diethyl ethyl-2-hexanamide.
- This formula product in fact exhales an original fragrance associating notes of rose thorn, eucaplyptus curve with a slightly peppery jasmine fragrance.
- the powerful, diffusive and voluminous character of its odor gives it a considerable and unique interest in the creation of compositions for perfumery in which it can be used as a single perfume or in combination with other compounds with different notes.
- perfumers in which N, N-diethyl ethyl-2 hexanamide can be advantageously used.
- Another example of compositions in which this compound can be advantageously introduced, is represented by the usual detergent compositions.
- compositions generally comprise one or more of the following ingredients: anionic, cationic or amphoteric surfactants, bleaching agents, optical brighteners, various fillers, anti-redeposition agents.
- anionic, cationic or amphoteric surfactants e.g., sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate
- N, N-diethyl ethyl-2 hexanamide is a colorless liquid, boiling at 87 ° C under a pressure of 1.5 mm of mercury, very soluble in the usual organic solvents such as alcohols, ketones, esters or ethers.
- N, N-2-ethyl-ethyl hexanamide 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 the 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-diethyl ethyl-2 hexanamide can be very high, for example greater than 50% by weight and can reach 90% by weight while in a perfume, a water toiletries, after shave lotion or soap, this content may be much less than 50% by weight.
- the lower limit of the content of N, N-diethyl ethyl-2 hexanamide 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 which are not within the limits of the contents indicated above without departing from the scope of the present invention.
- N, N-diethyl 2-ethylhexanamide can be prepared without difficulty by reaction of a 2-ethylhexanoyl halide with diethylamine in the presence of an alkaline base in aqueous solution (soda or potash).
- the DEH brings in this floral base a finely flowery, rosy note by exhaling the absolute of rose and by giving the jasmine note a remarkable natural character.
- a peppery base was prepared having the following composition:
- the DEH exhales in this composition the apparent concentration of the peppery note by adding to it a galbule note of eucalyptus and peppery rosebud.
- the DEH gives this base an exceptional character of lilac bouquet linked to the natural freshness of its floral note, to the heady and rising of eucalyptus and to the dewy note of lilac.
- the DEH used in the previous examples is a colorless liquid, with a boiling point of 87 ° C. under a pressure of 1.5 mm of mercury; its density at 20 ° C is 0.869 and its refractive index of 1.447.
- This product was obtained as follows:
- N, N-diethyl ethyl-2 hexanamide attenuates the artificial character of the base and brings to the composition the natural note of the ripe lemon skin.
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Beans For Foods Or Fodder (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT80420040T ATE650T1 (de) | 1979-04-02 | 1980-03-27 | 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 |
|---|---|---|---|
| FR7908693 | 1979-04-02 | ||
| FR7908693A FR2452921A1 (fr) | 1979-04-02 | 1979-04-02 | Procede d'obtention de compositions parfumantes et de produits parfumes et compositions et produits ainsi obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0017604A1 true EP0017604A1 (de) | 1980-10-15 |
| EP0017604B1 EP0017604B1 (de) | 1982-02-03 |
Family
ID=9224023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80420040A Expired EP0017604B1 (de) | 1979-04-02 | 1980-03-27 | Verfahren zur Herstellung parfümierender Zusammensetzungen und parfümierter Produkte und so erhaltene Zusammensetzungen und Produkte |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4301021A (de) |
| EP (1) | EP0017604B1 (de) |
| JP (1) | JPS55133307A (de) |
| AT (1) | ATE650T1 (de) |
| CA (1) | CA1146075A (de) |
| DE (1) | DE3060171D1 (de) |
| FR (1) | FR2452921A1 (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050577A3 (en) * | 1980-09-26 | 1982-09-08 | Rhone-Poulenc Specialites Chimiques | Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained |
| EP0051546A3 (en) * | 1980-09-26 | 1982-09-08 | Rhone-Poulenc Specialites Chimiques | Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained |
| EP0039032A3 (de) * | 1980-04-28 | 1982-09-15 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von 3,5,5-Trimethylhexansäureamiden als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4331550A (en) * | 1980-07-17 | 1982-05-25 | International Flavors & Fragrances Inc. | Carboamidoalkyl norbornanes and organoleptic use in detergents |
| US4331570A (en) * | 1980-07-17 | 1982-05-25 | International Flavors & Fragrances Inc. | Carboamidoalkyl norbornanes and organoleptic use in perfumes |
| US5143900A (en) * | 1989-05-19 | 1992-09-01 | Colgate-Palmolive Company | Perfumes containing N-lower alkyl neoalkanamide (s) |
| EP0651051A3 (de) * | 1993-10-29 | 1996-02-28 | Clorox Co | Auf Hypochloriten basierender gelförmiger Reiniger. |
| US7632972B2 (en) * | 2003-10-30 | 2009-12-15 | The Board Of Trustees Of The University Of Illionis | Compounds and methods for treatment of cancer and modulation of programmed cell death for melanoma and other cancer cells |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1572332A (de) * | 1968-04-05 | 1969-06-27 | ||
| FR2180942A1 (de) * | 1972-04-18 | 1973-11-30 | Wilkinson Sword Ltd |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788461A (fr) * | 1971-09-06 | 1973-03-06 | Givaudan & Cie Sa | Nouvelle substance odoriferante et aromatisante |
| GB1434728A (en) * | 1972-09-27 | 1976-05-05 | Wilkinson Sword Ltd | Compositions and articles containing phospine oxides having a physiological cooling effect and phosphine oxides for use therein |
-
1979
- 1979-04-02 FR FR7908693A patent/FR2452921A1/fr active Granted
-
1980
- 1980-03-27 AT AT80420040T patent/ATE650T1/de not_active IP Right Cessation
- 1980-03-27 EP EP80420040A patent/EP0017604B1/de not_active Expired
- 1980-03-27 DE DE8080420040T patent/DE3060171D1/de not_active Expired
- 1980-04-01 JP JP4125180A patent/JPS55133307A/ja active Granted
- 1980-04-01 CA CA000349006A patent/CA1146075A/fr not_active Expired
- 1980-04-02 US US06/136,545 patent/US4301021A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1572332A (de) * | 1968-04-05 | 1969-06-27 | ||
| FR2180942A1 (de) * | 1972-04-18 | 1973-11-30 | Wilkinson Sword Ltd |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039032A3 (de) * | 1980-04-28 | 1982-09-15 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von 3,5,5-Trimethylhexansäureamiden als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen |
| EP0050577A3 (en) * | 1980-09-26 | 1982-09-08 | Rhone-Poulenc Specialites Chimiques | Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained |
| EP0051546A3 (en) * | 1980-09-26 | 1982-09-08 | Rhone-Poulenc Specialites Chimiques | Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0017604B1 (de) | 1982-02-03 |
| ATE650T1 (de) | 1982-02-15 |
| DE3060171D1 (en) | 1982-03-11 |
| CA1146075A (fr) | 1983-05-10 |
| FR2452921A1 (fr) | 1980-10-31 |
| US4301021A (en) | 1981-11-17 |
| JPS6341366B2 (de) | 1988-08-17 |
| JPS55133307A (en) | 1980-10-17 |
| FR2452921B1 (de) | 1982-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Designated state(s): AT BE CH DE GB IT LU NL SE |
|
| 17P | Request for examination filed |
Effective date: 19801029 |
|
| ITF | It: translation for a ep patent filed | ||
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Designated state(s): AT BE CH DE GB IT LU NL SE |
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