EP0017604A1 - Process for producing perfuming compositions and perfumed products, and compositions and products so obtained - Google Patents
Process for producing perfuming compositions and perfumed products, and compositions and products so obtained Download PDFInfo
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- 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
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- 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.
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- 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)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
La présente invention a pour objet un procédé d'obtention de compositions parfumantes et de produits parfumés et les compositions et produits ainsi obtenus.The subject of the present invention is a process for obtaining perfume compositions and perfumed products and the compositions and products thus obtained.
On a déjà proposé l'utilisation de quelques amides d'acides alcanoïques en parfumerie ou dans des compositions répulsives contre les insectes, mais aucun de ces alcanamides ne s'est signalé par des propriétés olfactives originales. Ainsi, EINHORN et al., Ber. 39 1223 (1906) ont rapporté que la N,N-diéthyl éthyl-2 butanamide possède une faible odeur rappelant celle du menthol ; dans le brevet français 1 572 332 on a indiqué que la N,N-diéthyl diméthyl propanamide présente une fragrance de menthe poivrée alors que la N,N-diméthyl éthyl-2 butanamide exhale une senteur de menthe naturelle. Dans le brevet américain 3 909 462 on a attribué à la N-phényl N-méthyl éthyl-2 butanamide une note pamplemousse, recherchée pour l'obtention d'arômes alimentaires, et herbacée rendant ce produit apte à la réalisation de bases pour parfums à note lavande. Enfin A.S. LUTTA et al., Entomol. Obozrenie 45 317-25 (1966) ont noté, dans une étude consacrée aux propriétés répulsives pour les insectes des alcanamides, l'odeur agréable de la N,N-diéthyl octanamide sans toutefois en préciser la note. On a constaté que cette amide possède une note faiblement épicée relativement banale. En définitive, on constate que les amides des acides alcanoïques en C5-C6 possèdent, à l'exception du N-phényl N-méthyl éthyl-2 butanamide, des notes menthées plus ou moins communes. En outre, pour un acide donné le caractère de la note varie suivant la nature des substituants présents sur l'atome d'azote sans que le sens de cette variation puisse être prévisible ; c'est ainsi que la N,N-diméthyl éthyl-2 butanamide présente une note menthe naturelle fraîche plus puissante que la N,N-éthyl amide homologue dont la note bien que menthée est plus faible et poivrée. De son côté la structure de l'acide influence notablement la fragrance de l'amide ; ainsi la N,N'-diéthylcaprylamide présente une note différente de la N,N-diéthyl éthyl-2 butanamide. Il résulte de ce qui précède qu'il est difficile sinon impossible pour l'homme de l'art de prévoir si une alcanamide donnée possédera ou non une odeur agréable du point de vue olfactif et quelle en sera la note.The use of a few amides of alkanoic acids has already been proposed in perfumery or in insect repellants, but none of these alkanamides has been reported by original olfactory properties. Thus, EINHORN et al., Ber. 39 1223 (1906) reported that N, N-diethyl 2-ethyl-butanamide has a weak odor reminiscent of menthol; in French patent 1,572,332 it has been indicated that N, N-diethyl dimethyl propanamide has a peppermint fragrance while N, N-dimethyl 2-ethyl butanamide exhales a scent of natural mint. In US patent 3,909,462, N-phenyl N-methyl-ethyl-2-butanamide has been assigned a grapefruit note, sought for obtaining food flavors, and herbaceous rendering this product suitable for the production of bases for perfumes with lavender note. Finally AS LUTTA et al., Entomol. Obozrenie 45 317-25 (1966) noted, in a study devoted to repellents for insects of alkanamides, the pleasant odor of N, N-diethyl octanamide without however specifying the note. It has been found that this amide has a relatively banal, slightly spicy note. Ultimately, it is found that 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. In addition, for a given acid, 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 the homologous N, N-ethyl amide whose note, although mint is weaker and peppery. For its part, the structure of the acid notably influences the fragrance of the amide; thus N, N'-diethylcaprylamide has a different note from N, N-diethyl ethyl-2 butanamide. he 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.
L'industrie de la parfumerie est constamment à la recherche de produits qui par l'originalité, le volume et la puissance de leur fragrance puissent conférer aux compositions dans lesquelles ils entrent un caractère tout à fait particulier. La présente invention concerne précisément l'emploi, en parfumerie, d'un tel composé.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.
Plus spécifiquement la présente invention a pour objet un procédé pour l'obtention de compositions parfumantes, de.substances parfumées ou de produits finis parfumés caractérisés en ce que l'on ajoute aux constituants usuels de ces compositions, substances ou produits finis, une quantité efficace de N,N-diéthyl éthyl-2 hexanamide.More specifically, 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.
La présente invention a encore pour objet des compositions parfumantes, produits et substances parfumés caractérisés en ce qu'ils comportent à titre de principe actif ayant une influence sur l'odeur une quantité efficace de N,N-diéthyl éthyl-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.
Ce produit de formule :
Par "compositions parfumantes", on désigne des mélanges de divers ingrédients tels que solvants, supports solides ou liquides, fixateurs, composés odorants divers, etc..., dans lesquels est incorporée la N,N-diéthyl éthyl-2 hexanamide, lesquels mélanges sont utilisés pour procurer à divers types de produits finis la fragrance recherchée. Les bases pour parfum constituent des exemples préférés de compositions parfumantes dans lesquelles la N,N-diéthyl éthyl-2 hexanamide peut être avantageusement utilisée. Un autre exemple de compositions dans lesquelles ce composé peut être introduit de façon avantageuse, est représenté par les compositions détergentes usuelles. Ces compositions comprennent généralement un ou plusieurs des ingrédients suivants : agents tensioactifs anioniques, cationiques ou amphotères, agents de blanchiment, azurants optiques, charges diverses, agents antiredéposition. La nature de ces divers composants n'est pas critique et la N,N-diéthyl éthyl-2 hexanamide peut être ajoutée à tout type de composition détergente. Les eaux de toilettes, les lotions après rasage, les parfums, les savons ou les produits déodorants par exemple sous forme d'aérosols, constituent des exemples de substances ou de produits finis dans lesquels la N,N-diéthyl éthyl-2 hexanamide apporte sa note originale.By "perfuming compositions" is meant mixtures of various ingredients such as solvents, solid or liquid carriers, fixatives, various odorous compounds, etc., in which N , N -2-ethyl-2-ethylhexanamide is incorporated, which mixtures are used to provide various types of finished products with the desired fragrance. Perfume bases are preferred examples of compositions 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. 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. The nature of these various components is not critical and N, N-diethyl ethyl-2 hexanamide 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-diethyl ethyl-2-hexanamide provides original note.
La N,N-diéthyl éthyl-2 hexanamide est un liquide incolore, bouillant à 87°C sous une pression de 1,5 mm de mercure, très soluble dans les solvants organiques usuels tels que les alcools, les cétones, les esters ou les éthers.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.
La teneur des compositions selon l'invention en N,N-diéthyl éthyl-2 hexanamide exprimée en pourcentage en poids dans la composition considérée dépend de la nature de ladite composition (base pour parfum ou eau de toilette par exemple) et de la puissance et de la nature de l'effet recherché au niveau du produit final. Il va de soi que dans une base pour parfum la teneur en N,N-diéthyl éthyl-2 hexanamide peut être très importante, par exemple supérieure à 50 % en poids et peut atteindre 90 % en poids tandis que dans ûn parfum, une eau de toilette, une lotion après rasage ou un savon, cette teneur pourra être très inférieure à 50 % en poids. Ainsi la limite inférieure de la teneur en N,N-diéthyl éthyl-2 hexanamide peut être celle qui provoque une modification perceptible à l'odorat de la fragrance ou de la note du produit fini. Dans certains cas, cette teneur minimale peut être de l'ordre de 0,01 % en poids. On peut évidemment faire appel à des teneurs non comprises dans les limites des teneurs indiquées ci-avant sans pour autant sortir du cadre de la présente invention.The content of the compositions according to the invention in 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. Thus 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. In certain cases, 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.
La N,N-diéthyl éthyl-2 hexanamide peut être préparée sans difficulté par réaction d'un halogénure d'éthyl-2 hexanoyle avec la diéthylamine en présence d'une base alcaline en solution aqueuse (soude ou potasse).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).
Les exemples suivants illustrent l'invention et montrent comment elle peut être mise en pratique.The following examples illustrate the invention and show how it can be practiced.
On a réalisé une base pour parfum à note florale ayant la composition suivante :
Le DEH apporte dans cette base florale une note finement fleurie, rosée en exhaltant l'absolue de rose et en conférant à la note jasmin un caractère naturel remarquable.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.
On a préparé une base poivrée ayant le composition suivante :
Le DEH exhalte dans cette composition la concentration apparente de la note poivrée en y ajoutant une note galbule d'eucalyptus et bouton de rose poivrée.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.
On a préparé une base lilas ayant la composition suivante :
Le DEH confère à cette base un caractère exceptionnel de bouquet de lilas lié à la fraîcheur naturelle de sa note fleurie, à celle capiteuse et montante de l'eucalyptus et à la note rosée du lilas.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.
Dans chacune des compositions décrites aux exemples 1 à 3, on a remplacé le DEH par le dipropylène glycol qui se comporte comme un solvant neutre. Dans chaque cas on a assisté à la disparition complète de la note conférée à la composition considérée par le DEH.In each of the compositions described in Examples 1 to 3, DEH was replaced by dipropylene glycol which behaves as a neutral solvent. In each case, we have witnessed the complete disappearance of the rating given to the composition considered by the DEH.
Dans chacune des compositions décrites aux exemples 1 à 3, on a remplacé le DEH par l'un des amides suivants :
- - N,N-diéthyl éthyl-2 butanamide
- - N,N-diéthyl diméthyl-2,2 propanamide
- - N,N-diméthyl éthyl-2 butanamide
- - N-phényl N-méthyl éthyl-2 butanamide
- - N,N-diéthyl caprylamide.
- - N, N-2-ethyl diethyl butanamide
- - N, N-2,2-dimethyl dimethyl propanamide
- - N, N-dimethyl-2-ethyl butanamide
- - N-phenyl N-methyl ethyl-2 butanamide
- - N, N-diethyl caprylamide.
Dans chaque cas la note apportée à la base considérée par le DEH a disparu pour faire place à des notes menthées ou camphrées plus communes.In each case the note brought to the base considered by the DEH disappeared to make way for more common mint or camphor notes.
Le DEH utilisé dans les exemples précédents est un liquide incolore, de point d'ébullition 87°C sous une pression de 1,5 mm de mercure ; sa densité à 20°C est de 0,869 et son indice de réfraction de 1,447. Ce produit a été obtenu de la façon suivante :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:
Dans un réacteur en acier inoxydable de 3,8 1, équipé d'une agitation mécanique, d'un thermomètre interne, d'une ampoule de coulée de 1 litre et refroidi par un courant d'eau, on charge 892 g d'eau. On met l'agitation en marche et on ajoute, en 40 minutes, 824 g de diéthylamine en maintenant la température au dessous de 20°C. On ajoute ensuite 824 g de chlorure d'éthyl-2 hexanoyle en 3 heures. On maintient l'agitation pendant 2 heures à température inférieure à 20°C, puis on sépare la couche organique et la lave, d'abord avec 300 ml de soude aqueuse à 10 % en poids puis par 200 ml de soude aqueuse à 5 % en poids. La couche organique est ensuite distillée. On recueille ainsi un produit que l'on traite par du charbon actif sous azote. Après filtration, on obtient 1033 g d'un produit ayant les caractéristiques rapportées ci-avant et dont l'analyse centésimale et le spectre infra-rouge correspondent à ceux du produit de formule :
On ajoute 150 de N,N-diéthyl éthyl-2 hexanamide à la base pour poudre à laver ci-dessous :
L'addition du N,N-diéthyl éthyl-2 hexanamide atténue le caractère artificiel de la base et apporte à la composition la note naturelle de la peau du citron mûr.The addition of 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.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT80420040T ATE650T1 (en) | 1979-04-02 | 1980-03-27 | PROCESSES FOR PREPARING PERFUMED COMPOSITIONS AND PERFUMED PRODUCTS AND COMPOSITIONS AND PRODUCTS OBTAINED THUS. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7908693 | 1979-04-02 | ||
| FR7908693A FR2452921A1 (en) | 1979-04-02 | 1979-04-02 | PROCESS FOR OBTAINING PERFUMING COMPOSITIONS AND PERFUMED PRODUCTS AND COMPOSITIONS AND PRODUCTS THUS OBTAINED |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0017604A1 true EP0017604A1 (en) | 1980-10-15 |
| EP0017604B1 EP0017604B1 (en) | 1982-02-03 |
Family
ID=9224023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80420040A Expired EP0017604B1 (en) | 1979-04-02 | 1980-03-27 | Process for producing perfuming compositions and perfumed products, and compositions and products so obtained |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4301021A (en) |
| EP (1) | EP0017604B1 (en) |
| JP (1) | JPS55133307A (en) |
| AT (1) | ATE650T1 (en) |
| CA (1) | CA1146075A (en) |
| DE (1) | DE3060171D1 (en) |
| FR (1) | FR2452921A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039032A2 (en) * | 1980-04-28 | 1981-11-04 | Henkel Kommanditgesellschaft auf Aktien | Use of 3,5,5-trimethylhexanoic acid amides as perfuming agents and compositions containing them |
| EP0050577A2 (en) * | 1980-09-26 | 1982-04-28 | Rhone-Poulenc Specialites Chimiques | Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained |
| EP0051546A2 (en) * | 1980-09-26 | 1982-05-12 | Rhone-Poulenc Specialites Chimiques | Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4331570A (en) * | 1980-07-17 | 1982-05-25 | International Flavors & Fragrances Inc. | Carboamidoalkyl norbornanes and organoleptic use in perfumes |
| US4331550A (en) * | 1980-07-17 | 1982-05-25 | International Flavors & Fragrances Inc. | Carboamidoalkyl norbornanes and organoleptic use in detergents |
| US5143900A (en) * | 1989-05-19 | 1992-09-01 | Colgate-Palmolive Company | Perfumes containing N-lower alkyl neoalkanamide (s) |
| EP0651051A3 (en) * | 1993-10-29 | 1996-02-28 | Clorox Co | Gelled hypochlorite-based cleaner. |
| 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 (en) * | 1968-04-05 | 1969-06-27 | ||
| FR2180942A1 (en) * | 1972-04-18 | 1973-11-30 | Wilkinson Sword Ltd |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788461A (en) * | 1971-09-06 | 1973-03-06 | Givaudan & Cie Sa | NEW ODORING AND FLAVORING SUBSTANCE |
| 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/en active Granted
-
1980
- 1980-03-27 AT AT80420040T patent/ATE650T1/en not_active IP Right Cessation
- 1980-03-27 DE DE8080420040T patent/DE3060171D1/en not_active Expired
- 1980-03-27 EP EP80420040A patent/EP0017604B1/en not_active Expired
- 1980-04-01 JP JP4125180A patent/JPS55133307A/en active Granted
- 1980-04-01 CA CA000349006A patent/CA1146075A/en 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 (en) * | 1968-04-05 | 1969-06-27 | ||
| FR2180942A1 (en) * | 1972-04-18 | 1973-11-30 | Wilkinson Sword Ltd |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039032A2 (en) * | 1980-04-28 | 1981-11-04 | Henkel Kommanditgesellschaft auf Aktien | Use of 3,5,5-trimethylhexanoic acid amides as perfuming agents and compositions containing them |
| EP0039032A3 (en) * | 1980-04-28 | 1982-09-15 | Henkel Kommanditgesellschaft auf Aktien | Use of 3,5,5-trimethylhexanoic acid amides as perfuming agents and compositions containing them |
| EP0050577A2 (en) * | 1980-09-26 | 1982-04-28 | Rhone-Poulenc Specialites Chimiques | Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained |
| EP0051546A2 (en) * | 1980-09-26 | 1982-05-12 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4301021A (en) | 1981-11-17 |
| JPS55133307A (en) | 1980-10-17 |
| FR2452921A1 (en) | 1980-10-31 |
| FR2452921B1 (en) | 1982-07-02 |
| EP0017604B1 (en) | 1982-02-03 |
| DE3060171D1 (en) | 1982-03-11 |
| JPS6341366B2 (en) | 1988-08-17 |
| ATE650T1 (en) | 1982-02-15 |
| CA1146075A (en) | 1983-05-10 |
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